Diisopropylethylamine → HCID 21341520, compound

HRID 2185505Notes

Reaction equation

[C:1]([O:5][C:6]([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:7])([CH3:4])([CH3:3])[CH3:2].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:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of N-tert-butoxycarbonyl-D-homophenylalanine (3.0 g, 10.7 mmol), methoxymethylamine hydrochloride (1.15 g, 1.1 eq.), PyBrop (5 g, 1 eq.), diisopropylethylamine (5.6 mL, 3 eq.) and dichloromethane (10 mL) was stirred at 25° C. for 10 hours, and the reaction mixture was poured into ethyl acetate and washed successively with water, 1 N 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 the title 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

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

Sources & evidence

ORD record: ord-7a9dd33327a94cdead3cb0128f4660f1
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399629B1

Reaction notes

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