2-Methyl-6-nitrobenzoic anhydride → HCID 86639720, compound

HRID 888678Notes

Reaction equation

HRID 888678 reaction equation
CC1C=CC=C([N+]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O.[OH:26][C@H:27]([C@H:32]([NH:36][C:37](=[O:98])[C@H:38]([NH:60][C:61](=[O:97])[C@H:62]([NH:67][C:68](=[O:96])[CH2:69][C@@H:70](O)/[CH:71]=[CH:72]/[CH2:73][CH2:74][S:75][C:76]([C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1)([C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1)[C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)[CH2:63][CH:64]([CH3:66])[CH3:65])[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.C(Cl)Cl.C1COCC1>[OH:26][C@@H:27]1[CH2:28][C:29](=[O:31])[O:30][C@H:70](/[CH:71]=[CH:72]/[CH2:73][CH2:74][S:75][C:76]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:89]2[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=2)[C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH2:69][C:68](=[O:96])[NH:67][C@H:62]([CH2:63][CH:64]([CH3:65])[CH3:66])[C:61](=[O:97])[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:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:37](=[O:98])[NH:36][C@@H:32]1[CH:33]([CH3:34])[CH3:35]

Participants

6

Reactant 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 86639718HCID 86639718, compound

Product 1

HCID 86639720HCID 86639720, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 2-methyl-6-nitrobenzoic anhydride (MNBA) (32.7 mg, 0.095 mmol) and DMAP (22.5 mg, 0.184 mmol) in CH2Cl2 (20 mL) was added dropwise a solution of acid 5C (76 mg, 0.075 mmol) in CH2Cl2/THF (2:1, 66 mL) over 3 hours. After a further 12 h the reaction was quenched by the addition of 1M HCl (30 mL). The organic phase was separated (extracting with CH2Cl2) and washed with sat NaHCO3 (30 mL), followed by brine (30 mL). The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. Purification by column chromatography on silica gel (eluent 40% EtOAc/Hexane) gave 6C (35 mg, 0.035 mmol, 47%) as a yellow oil.

Workup

  1. customAfter a further 12 h the reaction was quenched by the addition of 1M HCl (30 mL)
  2. customThe organic phase was separated
  3. extraction(extracting with CH2Cl2)
  4. washwashed
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customPurification by column chromatography on silica gel (eluent 40% EtOAc/Hexane)

Sources & evidence

ORD record
ord-290d45e627774de3ac55d051a52089ba
Source dataset
uspto-grants-2012_08
Patent number
US08247372B2

Reaction notes

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