Hydrochloric Acid → 1-(N-benzyloxycarbonyl-2(S)-aminobutyryl)-L-proline

HRID 2185662Notes

Reaction equation

HRID 2185662 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C([O-])(O)=O.[Na+].[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][CH3:30])[C:26](O)=[O:27])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O.C(COC)OC>[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][CH3:30])[C:26]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:27])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 145742L-ProlineHCID 516892Sodium BicarbonateHCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

Product 1

HCID 213449341-(N-benzyloxycarbonyl-2(S)-aminobutyryl)-L-proline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2.1395 g of L-proline (18.6 mmol) and 1.56 g of NaHCO3 (18.6 mmol) in water (20 ml) is treated with a solution of 4.138 g of the succinimide ester of N-benzyloxycarbonyl-2(S)-aminobutyric acid (12.4 mmol) prepared as in Example 3 b), in dimethoxyethane (25 ml). After 5 hours, 12.4 ml of water are added, the resulting mixture is acidified to pH=2 with concentrated HCl and is extracted with ethyl acetate. The extracts are dried and are evaporated, which leads to a syrup.

Workup

  1. extractionis extracted with ethyl acetate
  2. customThe extracts are dried
  3. customare evaporated

Sources & evidence

ORD record
ord-33b4f9404324485f9230fb6cbec40f16
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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