Triethylamine → (S)-Methanesulphonic acid 2-Boc-aminopropyl ester

HRID 1774642Notes

Reaction equation

HRID 1774642 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].CCN(CC)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([O:1][CH2:2][C@@H:3]([NH:5][C:6]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:12])[CH3:4])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled mixture of (S)-tert-butyl 1-hydroxypropan-2-ylcarbamate (3.0 g, 17.1 mmol) and Et3N (4.8 mL, 34.2 mmol) in DCM (50 mL) was added methanesulfonyl chloride, MsCl (1.33 mL, 17.1 mmol) dropwise. The reaction mixture was stirred at rt for 2 h, diluted with DCM, washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give 107a (3.72 g, 86%) as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 4.044-4.033 (d, 2H), 3.164 (s, 3H), 1.385 (s, 9H), 1.065-1.051 (d, 3H)

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89704c5985204b52b4316775a33e7772
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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