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

HRID 872558Notes

Reaction equation

HRID 872558 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].C(N(CC)CC)C.[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 chlorideHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

(S)-tert-Butyl 1-hydroxypropan-2-ylcarbamate (10.25 g, 58.5 mmol) was dissolved DCM (20 ml). Triethylamine (12.23 ml, 87.7 mmol) was added and the solution was cooled to 0° C. under nitrogen. Methanesulfonylchloride (5.0 ml, 64.3 mmol) was diluted with DCM (5 ml) and added drop wise to the reaction mixture keeping the temperature under 10° C. After addition, the reaction mixture was allowed to warm up to RT and stirring was continued for 36 h. Next, the reaction mixture was diluted with DCM (150 ml) and washed several times with NaHCO3-solution and water, the organic layer dried with Na2SO4, filtered and evaporated affording 8.78 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.06 (d, 3H), 1.38 (s, 9H), 3.16 (s, 3H), 3.75 (m, 1H), 4.04 (m, 2H), 6.93 (m, 1H).

Workup

  1. additionadded drop wise to the reaction mixture
  2. customunder 10° C
  3. additionAfter addition
  4. temperatureto warm up to RT
  5. washwashed several times with NaHCO3-solution and water
  6. dry with materialthe organic layer dried with Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7d6b628b9eb347ed90ea7a4d646d0a17
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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