Ethyl 1H-pyrrole-3-carboxylate → 3-(1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrrol-3-yl)propanoic acid

HRID 254927Notes

Reaction equation

HRID 254927 reaction equation
C(OC([C:6]1[CH:10]=[CH:9][N:8]([CH2:11][C@@H:12]([C@H:22]([O:34][Si](C(C)(C)C)(C)C)[C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([CH3:31])=[C:25]([O:32][CH3:33])[CH:24]=2)[CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1)=O)C.C([O:44][C:45]([C:47]1C=CN[CH:48]=1)=[O:46])C.C(OC(C1C=NN(C[C@@H]([C@H](O[Si](C(C)(C)C)(C)C)C2C=C(OC)C(C)=C(OC)C=2)CCCC2C=CC=CC=2)C=1)=O)C>>[CH3:30][O:29][C:27]1[CH:28]=[C:23]([C@@H:22]([OH:34])[C@@H:12]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][N:8]2[CH:9]=[CH:10][C:6]([CH2:48][CH2:47][C:45]([OH:46])=[O:44])=[CH:7]2)[CH:24]=[C:25]([O:32][CH3:33])[C:26]=1[CH3:31]

Participants

4

Reactant 3

HCID 13070719Ethyl 1H-pyrrole-3-carboxylateHCID 66862796ethyl1-{(2S)-2-[(S)-{[tert-butyl(dimethyl)silyl]oxy}(3,5-dimethoxy-4-methylphenyl)methyl]-5-phenylpentyl}-1H-pyrazole-4-carboxylateHCID 66862874ethyl1-{(2S)-2-[(S)-{[tert-butyl(dimethyl)silyl]oxy}(3,5-dimethoxy-4-methylphenyl)methyl]-5-phenylpentyl}-1H-pyrrole-3-carboxylate

Product 1

HCID 668617593-(1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrrol-3-yl)propanoic acid

Procedure

Using ethyl1-{(2S)-2-[(S)-{[tert-butyl(dimethyl)silyl]oxy}(3,5-dimethoxy-4-methylphenyl)methyl]-5-phenylpentyl}-1H-pyrrole-3-carboxylate (produced by carrying out procedures similar to Example 24 using the compound produced in Example 16 and ethyl1H-pyrrole-3-carboxylate) instead of ethyl1-{(2S)-2-[(S)-{[tert-butyl(dimethyl)silyl]oxy}(3,5-dimethoxy-4-methylphenyl)methyl]-5-phenylpentyl}-1H-pyrazole-4-carboxylate, procedures similar to Example 29→Example 33→Example 34→Example 36→Example 37 were carried out to give the title compound having the following physical properties.

Workup

  1. customproduced

Sources & evidence

ORD record
ord-d6a656156f584ddaa020e86450795e36
Source dataset
uspto-grants-2011_01
Patent number
US07875745B2

Reaction notes

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