Trifluoroacetic acid → (2S)-N-[[1-(S-Benzoyl-3-mercaptopropanoyl)-5-(2-hydroxyphenyl)-2-pyrrolidinyl]carbonyl]phenylalanine

HRID 2295522Notes

Reaction equation

C([O:5][C:6](=[O:43])[C@H:7]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[N:12]1[C:23](=[O:35])[CH2:24][CH2:25][S:26][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[C:27]([S:26][CH2:25][CH2:24][C:23]([N:12]1[CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])[CH2:14][CH2:15][C@H:11]1[C:9]([NH:8][C@H:7]([C:6]([OH:43])=[O:5])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:10])=[O:35])(=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 86739178(2S)-N-[[1-(S-Benzoyl-3-mercaptopropanoyl)-5-(2-hydroxyphenyl)-2-pyrrolidinyl]carbonyl]phenylalanine t-butyl ester

Product 1

HCID 86739180(2S)-N-[[1-(S-Benzoyl-3-mercaptopropanoyl)-5-(2-hydroxyphenyl)-2-pyrrolidinyl]carbonyl]phenylalanineYield 79%

Procedure

The mixture of 0.7 g of (2S)-N-[[1-(S-benzoyl-3-mercaptopropanoyl)-5-(2-hydroxyphenyl)-2-pyrrolidinyl]carbonyl]-phenylalanine t-butyl ester obtained in Example 15, 2.7 g of trifluoroacetic acid and 0.6 g of anisole is stirred at room temperature for 4 hours. After removing trifluoroacetic acid and anisole from it, the reaction mixture is purified by silica gel column chromatography to give 0.5 g (79%) of the titled compound.

Workup

customAfter removing trifluoroacetic acid and anisole from it
customthe reaction mixture is purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b877d1cd1b384a719fd55ba408e6ff0d
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04425333

Reaction notes

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