Penicillin G → (S)-ethyl-3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate

HRID 323536

반응식

HRID 323536 반응식
[O:1]([CH2:8][C:9]([NH:11][CH:12]([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O>P([O-])([O-])([O-])=O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C@H:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[CH3:18]

참가 물질

5

반응물 3

HCID 5904Penicillin GHCID 14798Sodium HydroxideHCID 20644236HCID 20644236, 화합물

생성물 1

HCID 54332815(S)-ethyl-3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate

시약·촉매·용매 1

HCID 1061Phosphate용매

실험 절차

Racemic ethyl 3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate (1g) was suspended in phosphate buffer (250 mL, 0.01 molar, prepared from 0.1 molar pH 7.24 solution obtained from sigma). The pH of the solution was adjusted 7.8 using dilute sodium hydroxide. Under slow stirring, 100 units of immobilized penicillin G acylase (Boehringer-Mannheim) was added. The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was extracted with ethyl acetate (75 mL×3). The organic extracts were combined, dried over sodium sulfate, filtered and evaporated to dryness to give the desired amide, (S)-ethyl-3-(phenoxyacetamido)-5-(trimethylsilyl)-4-pentynoate. The immobilized enzyme was filtered off from the aqueous phase using Whatman No.1 filter paper. The pH of the aqueous phase was adjusted to 8.0 using dilute sodium hydroxide, and extracted with ethyl acetate (75 mL×3). The extracts were combined, dried over sodium sulfate, filtered and evaporated to dryness to give the desired amine, (R)-ethyl-3-amino-5-(trimethylsilyl)-4-pentynoate.

후처리

  1. extractionThe reaction mixture was extracted with ethyl acetate (75 mL×3)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-a134e06962504c938f001d697517685b
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214609B1

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