Ammonia → HCID 59248999, compound

HRID 552274Notes

Reaction equation

HRID 552274 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([CH3:29])=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:22]=2)=[O:17])[CH:5]=[C:6]([CH3:13])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][O:11]1.[NH3:30]>CO>[NH2:30][CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[C:6]([CH3:13])=[CH:5][C:4]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([CH3:29])=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:22]=2)=[O:17])=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86640169HCID 86640169, compound

Product 1

HCID 59248999HCID 59248999, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one (30 mg, 74 μmol) in methanol (1 mL) and ammonia (22 μL, approx. 7 N solution in methanol) is stirred at 65° C. for 4 h and at rt for 18 h. The solvent is removed in vacuo and the residue is purified by prep. HPLC to give 3-[4-(3-amino-2-hydroxy-propoxy)-3,5-dimethyl-phenyl]-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one (4 mg) as a colourless resin; LC-MS: tR=0.87 min, [M+1]+=424.24.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by prep

Sources & evidence

ORD record
ord-97e6a6004b09423db9fda7699f488802
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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