(2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester → 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl ester

HRID 1443447Notes

Reaction equation

HRID 1443447 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]([C:11]([OH:13])=O)[CH2:7][C@H:8]([OH:10])[CH:9]=1)=[O:4].[C:14]([O:18][C:19]([C@@:21]1([NH2:26])[CH2:23][C@H:22]1[CH:24]=[CH2:25])=[O:20])([CH3:17])([CH3:16])[CH3:15].C(OC(N1C[C@H](O)C[C@H]1C(=O)N[C@@]1(C(OCC)=O)C[C@@H]1C=C)=O)(C)(C)C>>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:11](=[O:13])[NH:26][C@:21]2([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:23][C@H:22]2[CH:24]=[CH2:25])[CH2:7][CH:8]([OH:10])[CH:9]=1)=[O:4]

Participants

4

Reactant 3

HCID 57563804(2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl esterHCID 68410381(1R,4S)-4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl esterHCID 68494585(1R,2S)-1-amino-2-vinyl-cyclo-propane carboxylic acid tert-butyl ester

Product 1

HCID 592041965-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-hydroxy-cyclopent-1-enecarboxylic acid methyl ester

Procedure

Reaction of compound 63 (50 mg, 37 mmol) with (1R,2S)-1-amino-2-vinyl-cyclo-propane carboxylic acid tert-butyl ester according to the method described for the preparation of 59 provided the title compound as a slightly yellow oil (50 mg, 38%).

Sources & evidence

ORD record
ord-a7434f9a84b04c93b2836b0d19f99619
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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