Methyl chloroformate → 1-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-methoxycarbonylamino-phenoxy)-2-propanol

HRID 1105822Notes

Reaction equation

HRID 1105822 reaction equation
[CH2:1]([N:8]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:9][CH:10]([OH:21])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[C:14]=1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:27]([O:29][CH3:30])=[O:28]>C(O)(C)C.O>[CH2:1]([N:8]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:9][CH:10]([OH:21])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:27]([O:29][CH3:30])=[O:28])[C:14]=1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 570867821-(N-benzyl-tert.-butylamino)-3-(3-amino-2-hydroxy-phenoxy)-2-propanol

Product 1

HCID 571804061-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-methoxycarbonylamino-phenoxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

14.5 g of 1-(N-benzyl-tert.-butylamino)-3-(3-amino-2-hydroxy-phenoxy)-2-propanol are dissolved in 140 ml of an isopropanol/water mixture (1:1) and 5.0 ml of methyl chloroformate are added, at 15°-20°, whilst stirring vigorously and stirring is continued for a further 11/2 hours at room temperature, the reaction mixture is then evaporated and the residue is dissolved in 50 ml of water. After extraction with 20 ml of ethyl acetate, the acid aqueous phase is rendered alkaline with concentrated sodium hydroxide solution and extracted with 3 times 100 ml of methylene chloride. Evaporation of the organic phase gives the crude base, from which crystalline 1-(N-benzyl-tert.-butylamino)-3-(2-hydroxy-3-methoxycarbonylamino-phenoxy)-2-propanol with a melting point of 130°-133° is isolated.

Workup

  1. stirringstirring
  2. custom2 hours
  3. customat room temperature
  4. customthe reaction mixture is then evaporated
  5. dissolutionthe residue is dissolved in 50 ml of water
  6. extractionAfter extraction with 20 ml of ethyl acetate
  7. extractionextracted with 3 times 100 ml of methylene chloride
  8. customEvaporation of the organic phase
  9. customgives the crude base

Sources & evidence

ORD record
ord-40d3b7338611416e85e1296e32cf0602
Source dataset
uspto-grants-1982_01
Patent number
US04310527

Reaction notes

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