Tert-butyl 2-(cyclopentylamino)acetate → HCID 20440242, compound

HRID 325483Notes

Reaction equation

HRID 325483 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=[S:7])(=[O:3])[CH3:2].[C:13]([O:17][C:18](=[O:26])[CH2:19][NH:20][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([O:17][C:18](=[O:26])[CH2:19][N:20]([C:6](=[S:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[C:1](=[O:3])[CH3:2])[CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1)([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 13298943Tert-butyl 2-(cyclopentylamino)acetateHCID 178466190HCID 178466190, compound

Product 1

HCID 20440242HCID 20440242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N1 -Dicyclohexylcarbodiimide (15.9 g, 77 mmol) in methylene chloride was added slowly to a mixture of 2-acetylthiobenzoic acid (15.2 g, 77 mmol) and N-cyclopentylglycine t-butyl ester (15.4 g) in methylene chloride maintained at 0°-5°. The mixture was brought to room temperature overnight, filtered, and the filtrate washed successively with dilute hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride solutions. After drying, the organic portion was concentrated, the residue dissolved in ether and the resulting solution filtered. Concentration of the filtrate gave crude N-(2-acetylthiobenzoyl)-N-cyclopentylglycine t-butyl ester as an oil.

Workup

  1. temperaturemaintained at 0°-5°
  2. filtrationfiltered
  3. washthe filtrate washed successively with dilute hydrochloric acid, saturated sodium bicarbonate and saturated sodium chloride solutions
  4. customAfter drying
  5. concentrationthe organic portion was concentrated
  6. dissolutionthe residue dissolved in ether
  7. filtrationthe resulting solution filtered

Sources & evidence

ORD record
ord-f4cb3b7f72694b61977dc7d0c5db4883
Source dataset
uspto-grants-1984_04
Patent number
US04440941

Reaction notes

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