Triphenylphosphine → (5)-Tert-butyl 3-(3-(chloromethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

HRID 1471637Notes

Reaction equation

HRID 1471637 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:50]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:50][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398Chlorosuccinimide2×HCID 90289960(5)-Tert-butyl 3-(3-(hydroxymethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 90289957(5)-Tert-butyl 3-(3-(chloromethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 3-(3-(hydroxymethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (1.0 g, 2.42 mmole) was dissolved in CH2Cl2 (5 ml). Triphenylphosphine (666 mg, 2.54 mmole) was added followed by N-chlorosuccinimide (355 mg, 2.66 mmole). After the vigorous reaction subsided, TLC showed ˜10% of unreacted starting material remained. Added 300 mg more N-chlorosuccinimide. TLC showed that the reaction was complete. The reaction mixture was purified without work-up by flash chromatography. Yield=1.0 g. MS (m/z) 433 [M+H]+.

Workup

  1. customAfter the vigorous reaction
  2. customThe reaction mixture was purified without work-up by flash chromatography

Sources & evidence

ORD record
ord-ec100825da0f4e45a76da6e638148730
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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