Triethylamine → (R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate
Reaction equation
CS(Cl)(=O)=O.O[CH2:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][O:10][CH3:11].CCN(CC)CC.[N-:27]=[N+:28]=[N-:29].[Na+]>C(Cl)Cl.CCOC(C)=O>[N:27]([CH2:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][O:10][CH3:11])=[N+:28]=[N-:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Methanesulfonyl chloride (4.0 g, 35 mmol) in DCM (50 mL) was slowly added to a solution of (R)-tert-butyl 1-hydroxy-3-methoxypropan-2-ylcarbamate (6.0 g, 29 mmol) and Et3N (3.64 g, 36 mmol) in DCM (150 mL) at 0° C. The reaction mixture was stirred at RT for 2 h. The organic phase was washed with water and saturated aq NaHCO3, concentrated, and dissolved in DMF. Sodium azide (2.34 g, 36.0 mmol) was added, and the reaction mixture was stirred at 75° C. for 4 h. The reaction mixture was diluted by EtOAc and washed with water. The crude product was purified by column chromatography on silica gel eluting with EtOAc and petroleum ether (EtOAc/PE=2/1) to give the title compound (4.3 g, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 4.92 (s, 1H), 3.91 (m, 1H), 3.53-3.48 (m, 2H), 3.45-3.40 (m, 2H), 3.38 (s, 3H), 1.47 (s, 9H).
Workup
- washThe organic phase was washed with water and saturated aq NaHCO3
- concentrationconcentrated
- dissolutiondissolved in DMF
- stirringthe reaction mixture was stirred at 75° C. for 4 h
- washwashed with water
- customThe crude product was purified by column chromatography on silica gel eluting with EtOAc and petroleum ether (EtOAc/PE=2/1)
Sources & evidence
- ORD record
- ord-8e04af24ea004419a37634aafeac2950
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181255B2
Reaction notes
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