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2-Methyl-6-nitrobenzoic anhydride → (3R,7S,10S,13R,14S)-7-benzyl-14-hydroxy-13-isopropyl-3-((E)-4-tritylsulfanyl-but-1-enyl)-10-tritylsulfanylmethyl-1,2-dioxa-4,9,12-triaza-cyclohexadecane-5,8,11,16-tetraone

HRID 888673
Notes
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Reaction equation

HRID 888673 reaction equation
CC1C=CC=C([N+]([O-])=O)C=1C(OC(C1C([N+]([O-])=O)=CC=CC=1C)=O)=O.[OH:26][C@H:27]([C@H:32]([NH:36][C:37](=[O:101])[C@H:38]([NH:60][C:61](=[O:100])[C@H:62]([CH2:70][C:71](=[O:99])[NH:72][C@H:73]([OH:98])/[CH:74]=[CH:75]/[CH2:76][CH2:77][S:78][C:79]([C:92]1[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=1)([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[CH2:39][S:40][C:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:33]([CH3:35])[CH3:34])[CH2:28][C:29]([OH:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:63]([C@@H:62]1[C:61](=[O:100])[NH:60][C@H:38]([CH2:39][S:40][C:41]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:37](=[O:101])[NH:36][C@H:32]([CH:33]([CH3:35])[CH3:34])[C@@H:27]([OH:26])[CH2:28][C:29](=[O:31])[O:30][O:98][C@H:73](/[CH:74]=[CH:75]/[CH2:76][CH2:77][S:78][C:79]([C:92]2[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=2)([C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)[C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[NH:72][C:71](=[O:99])[CH2:70]1)[C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 86639715(3S,4R)-3-hydroxy-4-((S)-2-{(S)-2-[((E)-(R)-1-hydroxy-5-tritylsulfanyl-pent-2-enylcarbamoyl)-methyl]-3-phenyl-propionylamino}-3-tritylsulfanyl-propionylamino)-5-methyl-hexanoic acid

Product 1

HCID 86639714(3R,7S,10S,13R,14S)-7-benzyl-14-hydroxy-13-isopropyl-3-((E)-4-tritylsulfanyl-but-1-enyl)-10-tritylsulfanylmethyl-1,2-dioxa-4,9,12-triaza-cyclohexadecane-5,8,11,16-tetraoneYield 61.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of MNBA (54 mg, 0.16 mmol) and DMAP (38 mg, 0.31 mmol) in CH2Cl2 (29 mL) was added dropwise a solution of the acid 5A (137 mg, 0.13 mmol) in CH2Cl2 (117 mL) over 4.5 h, this was then stirred overnight at room temperature. The reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL) before being dried (MgSO4), filtered and concentrated in vacuo to give a brown solid. Purification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3) gave 6A (79.4 mg, 0.08 mmol, 58%) as a white/brown solid: Rf 0.14 EtOAc/Hexane (4:6).

Workup

  1. washThe reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid
  6. customPurification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3)

Sources & evidence

ORD record
ord-68cc2c44f0784ad9babe48ce1c1c8577
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08247372B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes