Dichloromethane → HCID 53954534, compound

HRID 487509Notes

Reaction equation

HRID 487509 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7](=[CH2:24])[CH:8](O)[CH:9]([NH:20][CH:21]=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2].C(Cl)Cl.S(Br)([Br:30])=O>O>[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:24][Br:30])=[CH:8][CH:9]([NH:20][CH:21]=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 68176Thionyl bromideHCID 18991514HCID 18991514, compound

Product 1

HCID 53954534HCID 53954534, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.5 g (31.3 mmol) of benzyl 6-acetoxy-2-formylamino-3-hydroxy-4-methylenehexanoate are dissolved in 100 ml of abs. CH2Cl2. Then 2.91 ml (37.6 mmol) of thionyl bromide are added to this solution at room temperature. After 2 hours, 80 ml of water are added and the mixture is stirred vigorously for 10 minutes. The organic phase is separated and washed once with water, once with a 1N solution of KHCO3 and twice with water. The aqueous phases are extracted twice with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated by evaporation, giving benzyl 6-acetoxy-4-bromomethyl-2-formylamino-hex-3-enoate as a yellowish-brown oil which is further reacted without purification.

Workup

  1. customThe organic phase is separated
  2. washwashed once with water, once with a 1N solution of KHCO3 and twice with water
  3. extractionThe aqueous phases are extracted twice with CH2Cl2
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-474f31fdc5de4b05aeefe372f680476c
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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