Ethyl 5-bromovalerate → HCID 22815604, compound

HRID 1153839Notes

Reaction equation

HRID 1153839 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3].[Na].Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].P([O-])(O)(O)=O.[Na+]>C(O)C.CS(C)=O>[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][S:9][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH2:7])[CH3:3]

Participants

7

Reactant 4

HCID 84580Ethyl 5-bromovalerateHCID 2723617Ethyl cysteinate hydrochlorideHCID 5360545SodiumHCID 23672064Monosodium phosphate

Product 1

HCID 22815604HCID 22815604, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

L-Cysteine ethyl ester hydrochloride (18.6 g; 0.10 mole) was added to a solution of sodium (4.6 g; 0.20 g.a) in ethanol (320 ml; absolute), stirred 15 minutes and then the solvent removed in vacuo. To a solution of the residual sodium salts in dry dimethylsulphoxide (200 ml) was added ethyl 5-bromovalerate (21.0 g; 0.10 mole) in a single portion with stirring. The reaction mixture was allowed to stand at room temperature overnight, warmed on a steam bath for 5 mins. and then poured onto water (300 ml) containing sodium dihydrogen phosphate (1 g). The oil was extracted with ether (3×), the combined extracts washed with water and dried over MgSo4. The solvent was removed in vacuo yielding the product as a pale yellow oil which was used in Example 70.

Workup

  1. customthe solvent removed in vacuo
  2. temperaturewarmed on a steam bath for 5 mins
  3. additionand then poured onto water (300 ml)
  4. extractionThe oil was extracted with ether (3×)
  5. washthe combined extracts washed with water
  6. customdried over MgSo4
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d0987d1657a54bd4b3d02196668db050
Source dataset
uspto-grants-1984_12
Patent number
US04486443

Reaction notes

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