HCID 13599173, compound → N-(3-mercapto-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester

HRID 543262Notes

Reaction equation

HRID 543262 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([C:14](=[O:22])[CH:15]([CH3:21])[CH2:16][S:17]C(=O)C)[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([C:14](=[O:22])[CH:15]([CH3:21])[CH2:16][SH:17])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 1

HCID 13599173HCID 13599173, compound

Product 1

HCID 13469597N-(3-mercapto-2-methylpropanoyl)-N-cyclopentylglycine t-butyl esterYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution containing 50 g (0.14 mol) of N-(3-acetylthio-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester in 700 ml of methanol was bubbled nitrogen gas for 10 minutes followed by ammonia gas for 30 minutes. After 30 minutes the mixture was concentrated in vacuo and the residue taken up in ethyl acetate. It was washed once with 3% aqueous HCl and once with water, dried over MgSO4, filtered, and concentrated in vacuo to yield an oily product. Purification via HPLC [15% ethyl acetate in hexanes] afforded 30 g (70%) of N-(3-mercapto-2-methyl-propanoyl)-N-cyclopentylglycine t-butyl ester as an oil.

Workup

  1. customwas bubbled nitrogen gas for 10 minutes
  2. concentrationAfter 30 minutes the mixture was concentrated in vacuo
  3. washIt was washed once with 3% aqueous HCl and once with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield an oily product
  8. customPurification via HPLC [15% ethyl acetate in hexanes]

Sources & evidence

ORD record
ord-b14897b205bf4a40bedf678558b91e01
Source dataset
uspto-grants-1987_04
Patent number
US04661515

Reaction notes

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