Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]- → 5-((1R)-2-{Benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamide

HRID 1825307Notes

Reaction equation

HRID 1825307 reaction equation
C(O[N:9]([C:12]1[CH:17]=[C:16]([C@@H:18]2[CH2:20][O:19]2)[CH:15]=[CH:14][CH:13]=1)[CH:10]=[O:11])C1C=CC=CC=1.[CH2:21]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][C:38]#[CH:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([N:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][C:38]#[CH:39])[CH2:20][C@@H:18]([C:16]1[CH:15]=[CH:14][C:13]([O:19][CH2:18][C:16]2[CH:17]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:12]([NH:9][CH:10]=[O:11])[CH:17]=1)[OH:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 22145668Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]-HCID 86760081benzyloxy-5-[(2R)-oxiran-2-yl]phenylformamide

Product 1

HCID 114439305-((1R)-2-{Benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamideYield 159.6%

Procedure

A stirred mixture of 2-(benzyloxy-5-[(2R)-oxiran-2-yl]phenylformamide (R Hett et al, Organic Process Research & Development, 1998, 2, 96-99) (8.6 g) and N-benzyl-6-(but-3-ynyloxy)hexan-1-amine (9.1 g) was heated at 120° for 2 h. The mixture was purified by chromatography (Merck 9385) eluting with cyclohexane/ethyl acetate (2:1) to give the title compound (13.47 g). LCMS RT=2.68 min.

Workup

  1. temperaturewas heated at 120° for 2 h
  2. customThe mixture was purified by chromatography (Merck 9385)
  3. washeluting with cyclohexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-f6583bd1abf84b58b96e7dc6bc002542
Source dataset
uspto-grants-2006_05
Patent number
US07045658B2

Reaction notes

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