((S)-1-Cyclopentylcarbamoyl-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester → (1R,2S)-1-{[(1R,2R,4S)-2-((S)-1-Cyclopentylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 2242436Notes

Reaction equation

HRID 2242436 reaction equation
C(O[C:6](=[O:21])[NH:7][C@H:8]([C:13](=[O:20])[NH:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.C(OC([C@@H:29]1[CH2:33][C@H:32]([O:34][C:35]2[C:44]3[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=3)[N:38]=[C:37]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:36]=2)[CH2:31][C@H:30]1[C:53](=[O:65])[NH:54][C@:55]1([C:60]([O:62][CH2:63][CH3:64])=[O:61])[CH2:57][C@H:56]1[CH:58]=[CH2:59])=O)(C)(C)C.C(OC([C@@]1(NC([C@@H]2C[C@@H](OC3C4C(=CC(OC)=CC=4)N=C(C4C=CC=CC=4)C=3)C[C@H]2C(=O)N[C@H](C(=O)N[C@@H](C2CCCCC2)C(=O)NC)C(C)(C)C)=O)C[C@H]1C=C)=O)C>>[CH2:63]([O:62][C:60]([C@@:55]1([NH:54][C:53]([C@@H:30]2[CH2:31][C@@H:32]([O:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=4)[N:38]=[C:37]([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[CH:36]=3)[CH2:33][C@H:29]2[C:6](=[O:21])[NH:7][C@H:8]([C:13](=[O:20])[NH:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[C:9]([CH3:10])([CH3:11])[CH3:12])=[O:65])[CH2:57][C@H:56]1[CH:58]=[CH2:59])=[O:61])[CH3:64]

Participants

4

Reactant 3

HCID 57892997((S)-1-Cyclopentylcarbamoyl-2,2-dimethyl-propyl)-carbamic acid tert-butyl esterHCID 59204175(1R,2R,4R)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl esterHCID 59204178(1R,2S)-1-{[(1R,2R,4S)-2-{(S)-1-[((S)-Cyclohexyl-methylcarbamoyl-methyl)-carbamoyl]-2,2-dimethyl-propylcarbamoyl}-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 11422715(1R,2S)-1-{[(1R,2R,4S)-2-((S)-1-Cyclopentylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterYield 63.2%

Procedure

Compound 51 (298 mg, 0.048 mmol) and 35 (16 mg, 0.054 mmol) was deprotected and coupled according to the method for the preparation of 39. Purification by HPLC (MeOH/H2O 90:10 with 0.2% triethylamine) gave 52 (22 mg, 63%) as a colorless solid.

Workup

  1. customPurification by HPLC (MeOH/H2O 90:10 with 0.2% triethylamine)

Sources & evidence

ORD record
ord-ed651543a6ab4f89a5b3d7dd52afe77f
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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