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Diisopropylcarbodiimide → 15-(benzyloxycarbonyl)pentadecyl 5-(Cbz-amino)-4-oxopentanoate

HRID 1771063
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HRID 1771063 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[C:27]([NH:37][CH2:38][C:39](=[O:45])[CH2:40][CH2:41][C:42](O)=[O:43])([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].N1(C2C=CN=CC=2)CCCC1.C(N=C=NC(C)C)(C)C>ClCCl>[C:27]([NH:37][CH2:38][C:39](=[O:45])[CH2:40][CH2:41][C:42]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])=[O:43])([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 12734DiisopropylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 113691045-(((Benzyloxy)carbonyl)amino)-4-oxopentanoic acidHCID 90034516Benzyl 16-hydroxyhexadecanoate

생성물 1

HCID 9003448615-(benzyloxycarbonyl)pentadecyl 5-(Cbz-amino)-4-oxopentanoate수율 29.2%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

This compound was prepared from the product of 15a (1.2 g; 3.2 mmol), 5-(Cbz-amino)-4-oxopentanoic acid (0.84 g; 3.2 mmol), 4-pyrrolidinylpyridine (50 mg), and N,N′-diisopropylcarbodiimide (0.50 g; 4.0 mmol) in dichloromethane (35 mL) according to Procedure D. The reaction time was 3 days. The crude product was purified on a 85×55 mm silica gel 60 column eluted with ethyl acetate-hexane (1:1) (1000 mL) collecting 13×50 mL fractions. Fractions containing the product (3-6) were evaporated and 0.57 g (29%) product was obtained (white solid, mp 78-81° C.).

후처리

  1. customThe crude product was purified on a 85×55 mm silica gel 60 column
  2. washeluted with ethyl acetate-hexane (1:1) (1000 mL)
  3. customcollecting 13×50 mL fractions
  4. additionFractions containing the product (3-6)
  5. customwere evaporated

출처 및 근거

ORD 기록
ord-9f42bb99b1f8488ea8b67cbcb295054f
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249086B2

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