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

HRID 231936

反応式

HRID 231936 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7a485f6d53ff404f95ed49cbab69faae
出典データセット
uspto-grants-1989_07
特許番号
US04849414

関連ノート

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