Tert-butyl 2-(cyclopentylamino)acetate → N-(2-Acetylthio-3-chlorobenzoyl)-N-cyclopentylglycine t-butyl ester

HRID 325494Notes

Reaction equation

HRID 325494 reaction equation
[C:1]([S:4][C:5]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)(=[O:3])[CH3:2].[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:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[C:13]([Cl:14])[C:5]=1[S:4][C:1](=[O:3])[CH3:2])[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 134204052-Acetylthio-3-chlorobenzoic acid

Product 1

HCID 13420406N-(2-Acetylthio-3-chlorobenzoyl)-N-cyclopentylglycine t-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Acetylthio-3-chlorobenzoic acid (11.5 g, 50 mmol) and N-cyclopentylglycine t-butyl ester (10.0 g, 50 mmol) in methylene chloride (350 ml) were cooled to 0°-5° C., and N,N1 -dicyclohexylcarbodiimide (10.3 g, 50 mmol) in methylene chloride (50 ml) was added. The mixture was stirred overnight. The DCC-urea was filtered and washed with CH2Cl2. The filtrate was then washed 2×125 ml 1 N HCl, 2×125 ml saturated NaHCO3, 2×125 ml brine, dried (MgSO4), filtered and concentrated to give 20.6 g of an oil. The crude product was used without further purification in the next step.

Workup

  1. filtrationThe DCC-urea was filtered
  2. washwashed with CH2Cl2
  3. washThe filtrate was then washed 2×125 ml 1 N HCl, 2×125 ml saturated NaHCO3, 2×125 ml brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9598beaf598949b6a406cc5eea8c6c49
Source dataset
uspto-grants-1984_04
Patent number
US04440941

Reaction notes

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