5-Bromothiophene-2-carboxylic acid → (R)-3-{[(5-bromo-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1162658Notes

Reaction equation

HRID 1162658 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[Br:15][C:16]1[S:20][C:19]([C:21](O)=[O:22])=[CH:18][CH:17]=1>>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C@H:3]([CH2:2][NH:1][C:21]([C:19]2[S:20][C:16]([Br:15])=[CH:17][CH:18]=2)=[O:22])[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 3491155-Bromothiophene-2-carboxylic acidHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 58748318(R)-3-{[(5-bromo-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

56.1 Using general procedure E, (R)-3-aminomethyl-1-N-tert-butoxycarbonyl-pyrrolidine was coupled with 5-bromothiophene-2-carboxylic acid to give (R)-3-{[(5-bromo-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. Yellow oil. MS 389.0 ([M+H]+)

Sources & evidence

ORD record
ord-f4494d26fc9d45a084b50f4af06405aa
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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