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

HRID 256327

反応式

HRID 256327 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=O)C>[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収率 60%

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), diphenyl phosphorylazide (3.6 ml, 16.5 mmole) and dry DMF (30 ml) at 0° C. (ice bath) in an argon atmosphere was treated with triethyl amine (2.1 ml, 15.2 mmole) and L-proline, phenylmethyl ester, hydrochloride salt (3.6 g, 15.0 mmole). After 24 hours, the reaction mixture was partitioned between EtOAc and H2O. The aqueous phase was back extracted, the organic extracts combined, washed with 5% KHSO4, brine, and evaporated. The residue (5.0 g) was chromatographed on silica (130 g) eluting with EtOAc/Hexane (1:1) to give the title compound (2.5 g, 9.0 mmole, 60% yield) as a white crystalline solid after evaporation, m.p. 86°-88° C.

後処理

  1. customthe reaction mixture was partitioned between EtOAc and H2O
  2. extractionThe aqueous phase was back extracted
  3. washwashed with 5% KHSO4, brine
  4. customevaporated
  5. customThe residue (5.0 g) was chromatographed on silica (130 g)
  6. washeluting with EtOAc/Hexane (1:1)

出典と根拠

ORDレコード
ord-2989a7e57e4042ce93191b50bf02066c
出典データセット
uspto-grants-1987_10
特許番号
US04703043

関連ノート

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