Thionyl Chloride → 3-t-Butylamino-2-hydroxypropyl 3,4-dibenzyloxybenzoate

HRID 1995104Notes

Reaction equation

HRID 1995104 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C:30]([NH:34][CH2:35][CH:36]([OH:39])[CH2:37]O)([CH3:33])([CH3:32])[CH3:31]>C1(C)C=CC=CC=1.C1COCC1.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]([O:14][CH2:37][CH:36]([OH:39])[CH2:35][NH:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 908313-(tert-Butylamino)propane-1,2-diolHCID 108541553,4-Bis(benzyloxy)benzoic acid

Product 1

HCID 204069453-t-Butylamino-2-hydroxypropyl 3,4-dibenzyloxybenzoateYield 107.9%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To 20 g (0.06 mole) of the 3,4-dibenzyloxybenzoic acid in 200 ml of toluene was added 60 g (0.33 mole) of thionyl chloride. The reaction mixture was evaporated to dryness in vacuo to give a solid; m.p. 85°-86°. The solid was dissolved in 100 ml of dry THF and added dropwise into a solution of 17.7 g (0.06 mole) 3-(t-butylamino)-1,2-propanediol in 50 ml of pyridine and 50 ml of toluene. The reaction mixture was stirred for 1 hour at 25° C. and partitioned between ether and 5% K2CO3 solution. The ether layer was evaporated to dryness to give 30 g of solid.

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. customto give a solid
  3. custompartitioned between ether and 5% K2CO3 solution
  4. customThe ether layer was evaporated to dryness

Sources & evidence

ORD record
ord-c73d252ecbee442dac749fe155668131
Source dataset
uspto-grants-1983_09
Patent number
US04402974

Reaction notes

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