Triethylamine → (2S)-2,4-Bis[(tert-butoxycarbonyl)amino]butyl methanesulphonate

HRID 269617Notes

Reaction equation

HRID 269617 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][C@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][OH:12])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(CC)CC)C>ClCCl>[CH3:22][S:23]([O:12][CH2:11][C@@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57440192HCID 57440192, compound

Product 1

HCID 86601681(2S)-2,4-Bis[(tert-butoxycarbonyl)amino]butyl methanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation takes place in analogy to Example 84A from 250 mg (0.81 mmol) of tert-butyl{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}carbamate (Example 89A) in 20 ml of dichloromethane with 110 mg (0.97 mmol) of methanesulfonyl chloride and 0.23 ml (1.6 mmol) of triethylamine. The product is reacted without further purification.

Workup

  1. customPreparation
  2. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-66dc4b91028b4aafb09346fd1ff872a6
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

Loading…