Triethylamine → Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

HRID 852624Notes

Reaction equation

HRID 852624 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:5])[CH3:4].CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:1][CH2:2][C:3]([NH:6][C:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:13])([CH3:4])[CH3:5])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 11659022Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl esterYield 108.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2-hydroxy-1,1-dimethylethyl)carbamate (5.1 g, 27 mmol, 1 equiv) in CH2Cl2 (100 ml) at room temperature were added NEt3 (11.3 ml, 81 mmol, 3 equiv) and methanesulfonyl chloride (28.3 mmol, 2.2 ml, 1.05 equiv) and the resulting solution was stirred for 2 h then partitioned between AcOEt and a saturated aqueous NaHCO3 solution. The two layers were separated and the organic phase dried over MgSO4 and concentrated in vacuo to give 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-methylpropyl methanesulfonate (D273) (7.8 g, 108%) as a yellow oil which was used in the next step without further purification.

Workup

  1. customthen partitioned between AcOEt
  2. customThe two layers were separated
  3. dry with materialthe organic phase dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae3e04e921db464293be9b993b391562
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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