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Triphenylphosphine → (S)-4-Azido-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester

HRID 851429
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HRID 851429 반응식
O[CH:2]1[CH2:6][N:5]([C:7](=[O:24])[CH2:8][P:9]([O:21][CH2:22][CH3:23])([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])[C@H:4]([C:25]([O:27][CH3:28])=[O:26])[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:48]=[N+:49]=[N-:50].C1C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C.N=[N+]=[N-]>C(#N)C>[N:48]([CH:2]1[CH2:6][N:5]([C:7](=[O:24])[CH2:8][P:9]([O:21][CH2:22][CH3:23])([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])[C@H:4]([C:25]([O:27][CH3:28])=[O:26])[CH2:3]1)=[N+:49]=[N-:50]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 11776Triphenylphosphine2회HCID 24530Hydrazoic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 70291861Hydrazoic acid benzeneHCID 131712757(S)-4-Hydroxy-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester

생성물 1

HCID 131712758
(S)-4-Azido-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

(S)-4-Hydroxy-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester (2.0 g), triphenylphosphine (2.57 g), 2.1 N hydrazoic acid/benzene (12 ml, >5 equivalents) and dry acetonitrile are stirred under argon at room temperature for 30 minutes. Diethylazocarboxylate (1.71 g) in acetonitrile (5 ml) is added dropwise over 30 minutes. After 18 hours the reaction is still incomplete (as shown by thin-layer chromatography) and triphenylphosphine (1 equivalent), diethylazocarboxylate (1 equivalent) and 2.1 N hydrazoic acid (6 ml) are added. After 4 hours the reaction is complete. Nitrogen is bubbled through the solution to remove excess hydrazoic acid and the solvent is stripped leaving an oil. The oil is chromatographed on 100 mg of silica gel, eluting first with ethyl acetate and then with 3% methanol/ethyl acetate to give 1.64 g of the title compound.

후처리

  1. waitAfter 4 hours the reaction is complete
  2. customNitrogen is bubbled through the solution
  3. customto remove excess hydrazoic acid
  4. customthe solvent is stripped leaving an oil
  5. customThe oil is chromatographed on 100 mg of silica gel
  6. washeluting first with ethyl acetate

출처 및 근거

ORD 기록
ord-fce53fada788401696cbf19d8552bdb7
출처 데이터셋
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04384123

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