L-(+)-Cysteine → HCID 20095511, compound

HRID 1770211Notes

Reaction equation

HRID 1770211 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][SH:14].C1C[O:21][CH2:20][CH2:19]1>O>[C:20]([N:11]1[CH:12]([C:15]([OH:17])=[O:16])[CH2:13][S:14][CH:9]1[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 5862L-(+)-CysteineHCID 7707BenzenepropanalHCID 8028Tetrahydrofuran

Product 1

HCID 20095511HCID 20095511, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10 g of 3-phenylpropionaldehyde in THF was added to a solution of 10 g of cysteine in water. The resulting solution was stirred for 1 hour and then concentrated in vacuo. The precipitate was filtered off and washed with water and diethyl ether. The solid substance was dissolved in water which contained 12.5 g of potassium carbonate. 7.8 g of acetic anhydride were added at 0° C. and the resulting was stirred for 1 hour, after which the mixture was acidified to pH=2 with dilute sulphuric acid. This mixture was stirred for 30 minutes. The precipitate was filtered off, washed with water and dried. Yield 90%.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationThe precipitate was filtered off
  3. washwashed with water and diethyl ether
  4. dissolutionThe solid substance was dissolved in water which
  5. addition7.8 g of acetic anhydride were added at 0° C.
  6. stirringthe resulting was stirred for 1 hour
  7. stirringThis mixture was stirred for 30 minutes
  8. filtrationThe precipitate was filtered off
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-48a628d7b4884f85bb5a8fbef2dcce94
Source dataset
uspto-grants-1995_01
Patent number
US05385922

Reaction notes

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