Benzene → [4-Azidomethyl-2-phenylbenzoyl]methionine methyl ester

HRID 325220Notes

Reaction equation

HRID 325220 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[NH:32]=[N+:33]=[N-:34].C1C=CC=CC=1.[CH3:41][O:42][C:43](=[O:66])[C@H:44]([CH2:62][CH2:63][S:64][CH3:65])[NH:45][C:46](=[O:61])[C:47]1[CH:52]=[CH:51][C:50]([CH2:53]O)=[CH:49][C:48]=1[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>O1CCCC1>[CH3:41][O:42][C:43](=[O:66])[C@H:44]([CH2:62][CH2:63][S:64][CH3:65])[NH:45][C:46](=[O:61])[C:47]1[CH:52]=[CH:51][C:50]([CH2:53][N:32]=[N+:33]=[N-:34])=[CH:49][C:48]=1[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

7

Reactant 5

HCID 241BenzeneHCID 11776TriphenylphosphineHCID 24530Hydrazoic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20622833[4-Hydroxymethyl-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 20622822[4-Azidomethyl-2-phenylbenzoyl]methionine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To triphenylphosphine (1.0 equivalent) in tetrahydrofuran (THF) at −78° C. is added diethyl azodicarboxylate (1.0 equivalent) in THF. To this mixture is added a solution of hydrazoic acid in benzene (2.0 equivalents) and then the resultant compound from Example 16D (1.0 equivalent). After one hour the mixture was warmed to room temperature, stirred until the reaction is judged complete by TLC analysis, evaporated and chromatographed on silica gel to afford the title product.

Workup

  1. customevaporated
  2. customchromatographed on silica gel

Sources & evidence

ORD record
ord-8969d3e9535d42e7aba4f1c6ec9df930
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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