2-Methyl-6-nitrobenzoic anhydride → HCID 86653394, compound

HRID 1915965Notes

Reaction equation

HRID 1915965 reaction equation
CC1C=CC=C([N+]([O-])=O)C=1C(OC(C1C([N+]([O-])=O)=CC=CC=1C)=O)=O.[C:26]([O:30][C:31](=[O:102])[CH2:32][CH2:33][C@H:34]([C:65](=[O:101])[NH:66][C@@H:67]([C:89](=[O:100])[NH:90][C:91]1([CH:94]([OH:99])[CH2:95][C:96](O)=[O:97])[CH2:93][CH2:92]1)[CH2:68][S:69][C:70]([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)[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[NH:35][C:36](=[O:64])[CH2:37][C@H:38]([OH:63])/[CH:39]=[CH:40]/[CH2:41][CH2:42][S:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([CH3:29])([CH3:28])[CH3:27]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:26]([O:30][C:31](=[O:102])[CH2:32][CH2:33][C@H:34]1[NH:35][C:36](=[O:64])[CH2:37][C@@H:38](/[CH:39]=[CH:40]/[CH2:41][CH2:42][S:43][C:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:63][C:96](=[O:97])[CH2:95][CH:94]([OH:99])[C:91]2([CH2:92][CH2:93]2)[NH:90][C:89](=[O:100])[C@@H:67]([CH2:68][S:69][C:70]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)([C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=2)[C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[NH:66][C:65]1=[O:101])([CH3:28])([CH3:29])[CH3:27]

Participants

5

Reactant 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 86653392HCID 86653392, compound

Product 1

HCID 86653394HCID 86653394, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of MNBA (303.7 mg, 0.882 mmol) and DMAP (215.6 mg, 1.76 mmol) in CH2Cl2 (135 mL) was added dropwise a solution of the acid 8 (787 mg, 0.731 mmol) in CH2Cl2 (550 mL) over 3 h, and the mixture was then stirred for 16 h; the mixture was subsequently concentrated in vacuo to furnish a brown solid. Purification by column chromatography on silica (eluant 0:1-1:99-2:98-3:97 MeOH/CH2Cl2) gave 9 (430.2 mg, 0.407 mmol, 56%) as a white solid. The diastereoisomers were separable by flash column chromatography, though were used as a mixture for the subsequent reaction.

Workup

  1. concentrationthe mixture was subsequently concentrated in vacuo
  2. customto furnish a brown solid
  3. customPurification by column chromatography on silica (eluant 0:1-1:99-2:98-3:97 MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2f29defd7aff4c3d9f8b1595e2854727
Source dataset
uspto-grants-2013_12
Patent number
US08614193B2

Reaction notes

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