Dicyclohexylcarbodiimide → N-Boc-p-hydroxyphenylglycine

HRID 1282868

반응식

HRID 1282868 반응식
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:18]=[CH:17][C:16](CO)=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:21]N1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(#N)C>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:18]=[CH:17][C:16]([OH:21])=[CH:15][CH:14]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 20564729N-t-butoxycarbonyl-p-hydroxymethylphenylglycine

생성물 1

HCID 21896684N-Boc-p-hydroxyphenylglycine수율 115.6%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of dl-N-t-butoxycarbonyl-p-hydroxymethylphenylglycine (3.0 g, 0.011 mole) and N-hydroxysuccinimide (1.25 g., 0.011 mole) in 10 ml dry tetrahydrofuran and 50 ml dry acetonitrile was added N,N'-dicyclohexylcarbodiimide (2.238 g., 0.011 mole). The mixture was stirred at room temperature overnight. The dicyclohexylurea was filtered off and the filtrate taken to dryness under reduced pressure. The resulting solid was triturated with ether and filtered to give the N-hydroxysuccinimide ester of N-t-butoxycarbonyl-p-hydroxyphenylglycine (3.4 g., 83 percent yield) m.p. 141°-148° dec.

후처리

  1. filtrationThe dicyclohexylurea was filtered off
  2. customThe resulting solid was triturated with ether
  3. filtrationfiltered

출처 및 근거

ORD 기록
ord-63952eb54f754c9092fc467e9cc3adbd
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03972919

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