2-Methyl-6-nitrobenzoic anhydride → HCID 86639580, compound

HRID 539137Notes

Reaction equation

HRID 539137 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:77])[C@H:38]([NH:40][C:41](=[O:76])[C@H:42]([NH:46][C:47](=[O:75])[CH2:48][C@H:49]([OH:74])/[CH:50]=[CH:51]/[CH2:52][CH2:53][S:54][C:55]([C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH:43]([CH3:45])[CH3:44])[CH3:39])[CH:33]([CH3:35])[CH3:34])[CH2:28][C:29]([OH:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl.C1COCC1.CN(C=O)C>[OH:26][C@H:27]1[CH2:28][C:29](=[O:31])[O:30][O:74][C@H:49](/[CH:50]=[CH:51]/[CH2:52][CH2:53][S:54][C:55]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH2:48][C:47](=[O:75])[NH:46][C@H:42]([CH:43]([CH3:44])[CH3:45])[C:41](=[O:76])[NH:40][C@H:38]([CH3:39])[C:37](=[O:77])[NH:36][C@@H:32]1[CH:33]([CH3:35])[CH3:34]

Participants

6

Reactant 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 59223153HCID 59223153, compound

Product 1

HCID 86639580HCID 86639580, compoundYield 19.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent2×

Procedure

To a solution of MNBA (73.5 mg, 0.21 mmol) and DMAP (51.9 mg, 0.42 mmol) in CH2Cl2/THF (33 mL, 2:1) was added dropwise a solution of acid 8 (129 mg, 0.18 mmol) in CH2Cl2/THF (134.5 mL, 2:1) with 3 drops of DMF over 4 h. After a further 16 h the reaction mixture were concentrated in vacuo. Purification by flash column chromatography on silica (eluent 1:0-98:2-96:4-94:6-92.8 CH2Cl2/MeOH) gave 9 (24.7 mg, 0.035 mmol, 17%) as a white solid: Rf 0.43 CH2Cl2/MeOH (90:10); IR (thin film) 3293 (b), 2963 (m), 1732 (m), 1660 (s), 1536 (m) cm−1.

Workup

  1. concentrationAfter a further 16 h the reaction mixture were concentrated in vacuo
  2. customPurification by flash column chromatography on silica (eluent 1:0-98:2-96:4-94:6-92.8 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-66273d4365f54c0e99f7c9ef6373f877
Source dataset
uspto-grants-2014_10
Patent number
US08865655B2

Reaction notes

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