Diisopropylethylamine → HCID 21341520, compound

HRID 2304863Notes

Reaction equation

HRID 2304863 reaction equation
[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:22][O:23][CH2:24][NH2:25].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.ClCCl>[CH3:22][O:23][CH2:24][NH:25][C:18](=[O:20])[C@@H:9]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 2755954Boc-D-homophenylalanineHCID 21959107Methoxymethanamine hydrochloride

Product 1

HCID 21341520HCID 21341520, compoundYield 195.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Boc-D-homophenylalanine (3.0 g), methoxymethylamine hydrochloride (1.15 g), PyBrop (5 g); diisopropylethylamine (5.6 mL), and dichloromethane (10 mL) was stirred at 25° C. for 10 h., and the reaction mixture was poured into ethyl acetate and washed successively with water, 1N HCl, sat. sodium bicarbonate and brine. The combined extracts was dried (Na2SO4) and concentrated in vacuo. Further purification by chromatography over silica gel (45% ethyl acetate/hexane) afforded titled compound (6.76 g) as a white solid: 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.85 (m, 1H), 2.04 (m, 1H), 2.72 (m, 2H), 3.17 (s, 3H), 3.63 (s, 3H), 4.69 (m, 1H), 5.25 (bd, 1H, NH), 7.20 (m, 3H), and 7.28 (m, 2H).

Workup

  1. washwashed successively with water, 1N HCl, sat. sodium bicarbonate and brine
  2. dry with materialThe combined extracts was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customFurther purification by chromatography over silica gel (45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f301b251f9d242adb8aed69fe4de9fdb
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

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