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

HRID 2121127Notes

Reaction equation

HRID 2121127 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-8e5a45dca4b54701be798d7c898de16c
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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