Trimethyl orthoformate → (2S)-1-(1-Benzhydryl-azetidin-3-ylideneamino)-3-(4-benzyloxy-phenoxy)-propan-2-ol

HRID 2300207Notes

Reaction equation

HRID 2300207 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:20])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[C:21]1([CH:27]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:28]2[CH2:31][C:30](=O)[CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.COC(OC)OC>CO>[CH:27]([N:28]1[CH2:31][C:30](=[N:1][CH2:2][C@H:3]([OH:20])[CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:8][CH:7]=2)[CH2:29]1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 12044729(2S)-1-amino-3-(4-benzyloxy-phenoxy)-propan-2-ol

Product 1

HCID 12044730(2S)-1-(1-Benzhydryl-azetidin-3-ylideneamino)-3-(4-benzyloxy-phenoxy)-propan-2-olYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2S)1-Amino-3-(4-benzyloxy-phenoxy)-propan-2-ol (1.64 g, 6 mmol) and 1-(diphenylmethyl)-3-azetidinone (1.19 g, 5 mmol) in methanol (20 ml) was treated with trimethylorthoformate (1.59 g, 15 mmol), and stirred at room temperature for 2 days. The resulting suspension was filtered, and the precipitate washed with 3×5 ml of methanol, and dried in vacuo to give 1.96 g of a white solid. The methanol filtrate was evaporated, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was filtered through a pad of silica gel, and eluted with 2×30 ml of ethyl acetate. The combined filtrate was evaporated, and the residue triturated with a mixture of ether and hexanes to give an additional 0.30 g of product; m.p. 141-142° C.; MS (ES) m/z 748 (MH+); HRMS (El) Calcd. for C32H32N2O3 (M+): 492.2413, Found: 492.2397.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe precipitate washed with 3×5 ml of methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-825b48ec01fa4cafa88411cbfaa1411c
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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