2-Chloro-6-methylbenzoic acid → (2S)-2-(2-chloro-6-methyl-benzoylamino)-3-[4-(4-methyl-1,3-dioxo-1,3-dihydroisoindole-2-yl)phenyl]propionic acid ethylester

HRID 271317Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:36]([O:38][C:39](=[O:61])[C@@H:40]([NH2:60])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N:48]2[C:56](=[O:57])[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][C:54]=3[CH3:58])[C:49]2=[O:59])=[CH:44][CH:43]=1)[CH3:37]>ClCCl.C(N(CC)CC)C>[CH2:36]([O:38][C:39](=[O:61])[C@@H:40]([NH:60][C:4](=[O:6])[C:3]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])[CH2:41][C:42]1[CH:43]=[CH:44][C:45]([N:48]2[C:56](=[O:57])[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][C:54]=3[CH3:58])[C:49]2=[O:59])=[CH:46][CH:47]=1)[CH3:37]

Participants

Conditions

Temperature: 45 °C

Procedure

The mixture of 88.2 mg of 2-chloro-6-methyl benzoic acid, 99.1 mg of 1-(3-dimehtylaminopropyl)-3-ethylcarbodiimide hydrochloride, 79.1 mg of 1-hydroxybenzotriazol hydrate, 107 μl of triethylamine, 100 mg of (2S)-2-amino-3-[4-(4-methyl-1,3-dioxo-1,3-dihydroisoindole-2-yl)phenyl] propionic acid ethylester hydrochloride and 1 ml of dichloromethane was stirred at 45° C. overnight. The mixture was purified by silica gel chromatography to obtain the title compound.

Workup

customThe mixture was purified by silica gel chromatography

Sources & evidence

ORD record: ord-ec3a57bbe2fa426fb62dad6b2b7ac4f2
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452905B2

Reaction notes

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