Triethylamine → HCID 86615896, compound

HRID 2219610Notes

Reaction equation

HRID 2219610 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:17][OH:18])[CH2:15][OH:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:15][O:16][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:17][O:18][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:10][CH:9]=1)=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59771240HCID 59771240, compound

Product 1

HCID 86615896HCID 86615896, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of [4-(2-hydroxy-1-hydroxymethyl-ethyl)-phenyl]-carbamic acid tert-butyl ester (267 mg, 1.00 mmol, as prepared in the previous step) in DCM (10 mL) and Et3N (0.35 mL, 2.5 mmol), methanesulfonyl chloride (MsCl) (0.15 mL, 2.0 mmol) was added dropwise at 0° C. The resulting mixture was stirred at RT for 30 min, diluted with DCM (100 mL) and washed with satd NaHCO3 (20 mL). The organic layer was separated, dried (Na2SO4) and concentrated to afford methanesulfonic acid 2-(4-tert-butoxycarbonylamino-phenyl)-3-methanesulfonyloxy-propyl ester, which was dried in vacuo and directly used in next step: Mass spectrum, (ESI, m/z): Calcd. for C16H25NO8S2, 446.1 (M+Na). found 446.0.

Workup

  1. washwashed with satd NaHCO3 (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f4a05a90b5a4c78855da4d8b4a423f1
Source dataset
uspto-grants-2008_08
Patent number
US07414050B2

Reaction notes

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