Triethylamine → (2S)-2,5-Bis[(tert-butoxycarbonyl)amino]pentyl methanesulphonate

HRID 269612Notes

Reaction equation

HRID 269612 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]([O:17][C:18](=[O:34])[NH:19][C@H:20]([CH2:32][OH:33])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([CH3:16])([CH3:15])[CH3:14]>ClCCl>[CH3:1][S:2]([O:33][CH2:32][C@@H:20]([NH:19][C:18]([O:17][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:34])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86601679tert-butyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)butyl]carbamate

Product 1

HCID 86601678(2S)-2,5-Bis[(tert-butoxycarbonyl)amino]pentyl methanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

103 mg (0.90 mmol) of methanesulfonyl chloride and 0.21 ml (1.5 mmol) of triethylamine are added to a solution of 240 mg (0.75 mmol) of tert-butyl[(1S)-4-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)butyl]carbamate (Example 83A) in 20 ml of dichloromethane, and the mixture is stirred at RT for 16 h. The mixture is diluted with dichloromethane and washed twice with 0.1N hydrochloric acid. The organic phase is dried over magnesium sulfate and evaporated to dryness in vacuo. The product is reacted without further purification.

Workup

  1. washwashed twice with 0.1N hydrochloric acid
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated to dryness in vacuo
  4. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-69c272a634874da0b578e392e1803026
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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