Dimethylformamide → O-(tert-Butyldimethylsilyl)-Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithinol

HRID 1067107Notes

Reaction equation

[CH2:1]([N:8]([CH3:23])[C@H:9]([CH2:21][OH:22])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[Si:29](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.O>[Si:29]([O:22][CH2:21][C@H:9]([CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:23])([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of Nα-benzyl-Nδ-Boc-Nα-methylornithinol (560 mg), dimethylformamide (1.5 ml), and t-butyldimethylsilyl chloride (330 mg), triethylamine (290 μl) and 4-(N,N-dimethylamino)pyridine (21 mg) was stirred at 0° C., under nitrogen atmosphere, for 1 hr. Then the mixture was stirred, at 25° C., for 10 hrs and then poured into water (20 ml) and extracted with dichloromethane (2×20 ml). The combined organic phase was washed with water and brine, and dried over sodium sulfate. Evaporation of the solvent afforded titled compound (690 mg) as a clear solid: 1H NMR (400 MHz, CDCl3) δ0.06 (s, 6H), 0.91 (s, 9H), 1.43 (s, 9H), 1.45-1.73 (m, 4H), 2.22 (s, 3H), 2.68 (m, 1H), 3.12 (m, 2H), 3.62 (dd, J=10.4; 5.2 Hz, 1H), 3.68 (d, J=13.6 Hz, 1H), 3.78 (m, 2H), and 7.30 (m, 5H).

Workup

extractionextracted with dichloromethane (2×20 ml)
washThe combined organic phase was washed with water and brine
dry with materialdried over sodium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-60cd06d9e152451fbb6c8d9273a5e895
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245746B1

Reaction notes

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