Hydrochloric Acid → HCID 86601806, compound

HRID 2235382Notes

Reaction equation

HRID 2235382 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][OH:15])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26].Cl>CCOC(C)=O>[C:1]([O:5][C:6]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15292992tert-Butyl [2-(hydroxymethyl)phenyl]carbamate

Product 1

HCID 86601806HCID 86601806, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-hydroxymethyl-phenyl)-carbamic acid tert-butyl ester (0.8 g; 3.6 mmol) in EtOAc (15 ml) at 0° C. is added NEt3 (610 μl) and methanesulfonyl chloride (340 μl). After addition the mixture is warmed to RT and stirred for 3 days. After completion the reaction mixture is acidified with diluted hydrochloric acid and extracted twice with EtOAc. The organic phase is washed with brine, dried over MgSO4 and evaporated to give methanesulfonic acid 2-tert-butoxycarbonylamino-benzyl ester (0.73 g).

Workup

  1. additionAfter addition the mixture
  2. extractionextracted twice with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-daf57e24bd564cb8a207d8823f1be636
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

Loading…