Ethyl bromoacetate → HCID 11027636, compound

HRID 380643Notes

Reaction equation

HRID 380643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:9]([O:11][CH2:12][C@@:13]2([OH:24])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[OH:23])[CH2:14]2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:9]([O:11][CH2:12][C@@:13]2([OH:24])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:23][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:14]2)=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11091194HCID 11091194, compound

Product 1

HCID 11027636HCID 11027636, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2R)-2-{[N,N-di(4-fluorophenyl)-carbamoyloxy]methyl}-2,5-dihydroxy-1,2,3,4-tetrahydro-naphthalene (0.18 g) and powder K2CO3 in dry DMF (1.8 ml) was added ethyl bromoacetate (0.047 ml) at room temperature. After stirring for 16 hours, the reaction mixture was partitioned between AcOEt and water. The organic layer was washed with water, brine, dried over MgSO4 and evaporated in vacuo. The residue was crystallized from n-hexane to give (2R)-2-{[N,N-di(4-flurophenyl)carbamoyloxy]methyl}-5-[(ethoxycarbonyl)methoxy]-2-hydroxy-1,2,3,4-tetrahydronaphthalene (0.16 g) as white solid.

Workup

  1. customthe reaction mixture was partitioned between AcOEt and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-12ef946b3a2e4a149cc74b710c04601c
Source dataset
uspto-grants-2001_10
Patent number
US06303649B1

Reaction notes

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