Water → HCID 59134397, compound

HRID 1993492Notes

Reaction equation

HRID 1993492 reaction equation
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[C:35]([O:36]C)=[CH:34][C:10]2[C@H:11]([N:18]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)C(=O)OC(C)(C)C)[C@@H:12]([OH:17])[C:13]([CH3:16])([CH3:15])[O:14][C:9]=2[CH:8]=1)(=[O:5])=[O:4].B(Br)(Br)Br.O>ClCCl>[Cl:1][CH2:2][S:3]([NH:6][C:7]1[C:35]([OH:36])=[CH:34][C:10]2[C@H:11]([NH:18][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@@H:12]([OH:17])[C:13]([CH3:16])([CH3:15])[O:14][C:9]=2[CH:8]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 59134381HCID 59134381, compound

Product 1

HCID 59134397HCID 59134397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of t-butyl(3R*,4S*)-7-{[(chloromethyl)sulfonyl]amino}-3-hydroxy-6-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl(2-phenylethyl)carbamate (400 mg, 0.72 mmol) in dichloromethane (4.0 mL), 1 mol/L solution of boron tribromide in dichloromethane (3.61 mL, 3.61 mmol) was added below freezing point, and the resulting mixture was stirred at 0° C. for 1 hour. Water was added, and the resulting mixture was further stirred for 30 minutes. The resulting solid was filtered off, washed with water and then with chloroform. The solid was dried at 60° C. for 3 hours under reduced pressure, and the aimed product was quantitatively obtained.

Workup

  1. stirringthe resulting mixture was further stirred for 30 minutes
  2. filtrationThe resulting solid was filtered off
  3. washwashed with water
  4. customThe solid was dried at 60° C. for 3 hours under reduced pressure

Sources & evidence

ORD record
ord-fc61bf57847d476db8377d601cb495b1
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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