Triethylamine → 1-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester

HRID 231936

반응식

HRID 231936 반응식
[C:1]([O-])(=[O:5])[CH:2]([CH3:4])[OH:3].[Na+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.Cl.[NH:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>CN(C)C=O>[OH:3][C@@H:2]([CH3:4])[C:1]([N:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])=[O:5]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2733413Proline benzyl ester hydrochlorideHCID 23666456Sodium Lactate

생성물 1

HCID 133352881-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of sodium lactate (1.7 g., 15.0 mmole), diphenylphosphorylazide (3.6 ml., 1.1 eq.), and dry dimethylformamide (30 ml.) at 0° (ice-bath) in an argon atmosphere is treated with triethylamine (2.1 ml., 1.0 eq.) and L-proline, phenylmethyl ester, monohydrochloride salt (3.6 g., 15.0 mmole). After 24 hours, the reaction mixture is partitioned between ethyl acetate and water. The aqueous phase is back extracted, the organic extracts are combined, washed with 5% potassium bisulfate, brine, and evaporated. The residue (5 g.) is chromatographed on silica (130 g.) eluting with (1:1, ethyl acetate/hexane) to give 2.5 g. of 1-[(S)-2-hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester as a white crystalline solid after evaporation; m.p. 86°-88° (isopropyl ether). TLC (silica gel; ethyl acetate) Rf =0.4.

후처리

  1. customthe reaction mixture is partitioned between ethyl acetate and water
  2. extractionThe aqueous phase is back extracted
  3. washwashed with 5% potassium bisulfate, brine
  4. customevaporated
  5. customThe residue (5 g.) is chromatographed on silica (130 g.)
  6. washeluting with (1:1, ethyl acetate/hexane)
  7. customto give 2.5 g
  8. customof 1-[(S)-2-hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester as a white crystalline solid after evaporation

출처 및 근거

ORD 기록
ord-7a485f6d53ff404f95ed49cbab69faae
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04849414

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