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

HRID 1771063Notes

Reaction equation

HRID 1771063 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-9f42bb99b1f8488ea8b67cbcb295054f
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

Loading…