Triethylamine → HCID 89486854, compound

HRID 878410Notes

Reaction equation

HRID 878410 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][O:5][CH3:6].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH2:2][C@@H:3]([NH:7][C:8]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:17])[CH2:4][O:5][CH3:6])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69024598HCID 69024598, compound

Product 1

HCID 89486854HCID 89486854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl [(2R)-1-hydroxy-3-methoxypropan-2-yl]carbamate (30 g, 0.13 mol) in DCM (300 mL) at 0° C. was added triethylamine (19.0 g, 0.188 mol) and methanesulfonylchloride (21.6 g, 0.188 mol) and then the reaction mixture was allowed to warm to ambient temperature. After 16 hours, the reaction mixture was washed with brine, and the organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether) to give (2S)-2-{[(benzyloxy)carbonyl]amino}-3-methoxypropyl methanesulfonate. MS ESI calc'd. for C13H20NO6S [M+H]+ 318. found 318. 1H NMR (400 MHz, CDCl3) δ 7.36-7.33 (m, 5H), 5.24 (d, J=8.0 Hz, 1H), 5.10 (s, 2H), 4.28 (d, J=5.6 Hz, 2H), 4.12-4.09 (m, 1H), 3.55-3.42 (m, 2H), 3.35 (s, 3H), 2.99 (s, 3H).

Workup

  1. washthe reaction mixture was washed with brine
  2. dry with materialthe organics were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-8bc937c253cc440cb2cad06afd82316e
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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