Carbon tetrabromide → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-4-bromomethylphenyl)-L-phenylalanine ethyl ester

HRID 253737Notes

Reaction equation

HRID 253737 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH2:32]OCC)=[CH:26][C:25]=2[O:36][CH3:37])=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:59]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:38])[C@H:5]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH2:32][Br:59])=[CH:26][C:25]=2[O:36][CH3:37])=[CH:20][CH:19]=1)[NH:6][C:7](=[O:16])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66843037HCID 66843037, compound

Product 1

HCID 54431777N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-4-bromomethylphenyl)-L-phenylalanine ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product obtained in Example 1 -(5) or Reference Example 3-(3) (3.0 g) in CH2Cl2 (80 ml) containing PPh3 (1.77 g) was added CBr4 (2.8 g) at 0° C. The mixture was stirred at room temperature for 3 hours and evaporated. The residue was purified by: column chromatography (silica gel; eluent:AcOEt/n-hexane 1:1) to yield N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-4-bromomethylphenyl)-L-phenylalanine ethyl ester (3.15 g). IR (Nujol) 1731, 1654 cm−1; MS (APCI) m/z 59.6 (M+H).

Workup

  1. customevaporated
  2. customThe residue was purified by: column chromatography (silica gel; eluent:AcOEt/n-hexane 1:1)

Sources & evidence

ORD record
ord-a9f4bb5e7d6a4a5ab3bd5b94b82c37aa
Source dataset
uspto-grants-2011_01
Patent number
US07872151B2

Reaction notes

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