Penicillin G → Ethyl 3-amino-4-pentynoate

HRID 323535

Reaction equation

HRID 323535 reaction equation
Cl.[NH2:2][CH:3]([C:10]#[CH:11])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O.C1(CC(OCC)=O)C=CC=CC=1.[OH-].[Na+]>O.C(#N)C>[NH2:2][CH:3]([C:10]#[CH:11])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 5904Penicillin GHCID 7590Ethyl phenylacetate3×HCID 14798Sodium HydroxideHCID 22006120Ethyl 3-amino-4-pentynoate hydrochloride

Product 1

HCID 22006121Ethyl 3-amino-4-pentynoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In water(30 mL) were mixed ethyl 3-amino-4-pentynoate hydrochloride (258.3 mg, 1.5 mmoles), 30.6 mg (3.95 units) immobilized penicillin G amidohydrolase [Rohm-Pharma] and ethyl phenylacetate (205.7 mg, 1.25 mmoles). The initial pH (3.48) was adjusted to pH 6 with N NaOH (0.5 N) before addition of the ethyl phenylacetate. After 3 hours, an additional 0.9 mmole ethyl phenylacetate was added. This suspension was stirred vigorously at room temperature for six hours. Periodically, 1 mL samples were taken and diluted with acetonitrile and analyzed by reversed phase HPLC.

Sources & evidence

ORD record
ord-f21da0992b6146d5812b6063358e7f09
Source dataset
uspto-grants-2001_04
Patent number
US06214609B1

Linked notes

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