Phenol → HCID 86613212, compound

HRID 1987162Notes

Reaction equation

HRID 1987162 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:8]=[N+:9]=[N-:10].[CH2:11]([C@H:18]([NH:25]C(=O)OC(C)(C)C)[C@@H:19](O)[CH2:20]CCC)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[N:8]([C@@H:19]([CH2:20][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C@@H:18]([NH2:25])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N+:9]=[N-:10]

Participants

5

Reactant 3

HCID 996PhenolHCID 24530Hydrazoic acidHCID 86613206tert-butyl (1S,2S)-1-benzyl-2-hydroxyhexylcarbamate

Product 1

HCID 86613212HCID 86613212, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared in a manner to similar to intermediate XXII. Step A employed DMF as solvent and 3 equiv of phenol as nucleophile. Steps B and C were substituted with Mitsunobu hydrazoic acid inversion (see Intermediate I step C): ES MS (M+H)=283.6.

Sources & evidence

ORD record
ord-798dd78d6a3f4ce9a6418207ebb2d79d
Source dataset
uspto-grants-2009_06
Patent number
US07550481B2

Reaction notes

Loading…