Benzyl chloroformate → HCID 54532864, compound

HRID 443421Notes

Reaction equation

HRID 443421 reaction equation
[NH2:1][CH:2]([CH3:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][N:5]=1.[C:12](=[O:15])([OH:14])[O-].[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>C(Cl)Cl>[C:12]([C:8]1[C:7]([OH:10])=[CH:6][N:5]=[C:4]([CH2:3][CH:2]([NH2:1])[CH3:11])[C:9]=1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])([O:14][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:15]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 15572412HCID 15572412, compound

Product 1

HCID 54532864HCID 54532864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting material is prepared as follows: To the solution of 0.5 g of 2-(2-aminopropyl)-5-pyridinol, 10 ml of methylene chloride and 10 ml of saturated aqueous sodium bicarbonate, 1.04 g of benzyl chloroformate are added while stirring at room temperature. After 12 hours the organic phase is separated, dried, evaporated and the residue crystallized from diethyl ether-hexane, to yield the bis-carbobenzyloxy-2-(2-aminopropyl)-5-pyridinol melting at 63°-65°.

Workup

  1. customThe starting material is prepared
  2. customAfter 12 hours the organic phase is separated
  3. customdried
  4. customevaporated
  5. customthe residue crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-401b574888304335ac22b6da12aeaa2f
Source dataset
uspto-grants-1981_04
Patent number
US04260619

Reaction notes

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