Tert-butyl 2-(cyclopentylamino)acetate → HCID 20465235, compound

HRID 325501Notes

Reaction equation

HRID 325501 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([OH:10])=O)[C:6]=1[OH:14])=[O:4].[C:15]([O:19][C:20](=[O:28])[CH2:21][NH:22][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[C:15]([O:19][C:20](=[O:28])[CH2:21][N:22]([C:8](=[O:10])[C:7]1[C:6](=[C:5]([C:3](=[O:4])[CH2:2][Cl:1])[CH:13]=[CH:12][CH:11]=1)[OH:14])[CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 13298943Tert-butyl 2-(cyclopentylamino)acetateHCID 20465232HCID 20465232, compound

Product 1

HCID 20465235HCID 20465235, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroacetylsalicylic acid was combined with N-cyclopentylglycine t-butyl ester and N,N1 -dicyclohexylcarbodiimide at 0° C. in methylene chloride as described in Example I. Similar workup gave crude N-(3-chloroacetylsalicyloyl)-N-cyclopentylglycine t-butyl ester, which was cleaved to N-(3-chloroacetylsalicyloyl)-N-cyclopentylglycine using iodotrimethylsilane prepared in situ as described in Example I. Hydrolysis with aqueous sodium hydroxide (Example IV) provided the title compound.

Sources & evidence

ORD record
ord-c4873401acee48838b7d6e2f4e8daaf2
Source dataset
uspto-grants-1984_04
Patent number
US04440941

Reaction notes

Loading…