Hydrochloric Acid → 3-(Benzyloxycarbonylamino) propionyl-L-histidine

HRID 467949노트

반응식

HRID 467949 반응식
[NH2:1][CH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:14]([OH:16])=[O:15])[CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)=[O:5].[OH-].[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].Cl>CC(C)=O.O>[CH2:23]([O:22][C:20]([NH:1][CH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:14]([OH:16])=[O:15])[CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)=[O:5])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2회HCID 439224Carnosine

생성물 1

HCID 1785208513-(Benzyloxycarbonylamino) propionyl-L-histidine수율 111.1%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
22.5 °C

실험 절차

A 0.5 L round-bottom flask is loaded with 22.6 g of 3-aminopropionyl-histidine, 150 ml of water and 30 ml of acetone. The solution is adjusted to pH 13.00 with 30% sodium hydroxide, then cooled to 0-5° C., at which temperature 18.7 g of benzyl chloroformate are dropwise added in about 1 h, keeping pH at 12-13 with sodium hydroxide. Afterwards, the mixture is stirred for 15 h at 20-25° C., acidified to pH 2.0-2.5 with 37% hydrochloric acid, then concentrated under vacuum, at 50° C. maximum, carrying out repeated evaporations with isopropanol to a white solid residue. 40 g of a residue are obtained.

후처리

  1. additionare dropwise added in about 1 h
  2. concentrationconcentrated under vacuum, at 50° C. maximum

출처 및 근거

ORD 기록
ord-e345d0d6f5fe49d4a556aefe468e6321
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623900B2

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