Dichloromethane → HCID 14505566, compound

HRID 1589319Notes

Reaction equation

HRID 1589319 reaction equation
[CH3:1][NH:2][C:3](=[O:28])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C(Cl)[Cl:37]>>[ClH:37].[CH3:1][NH:2][C:3](=[O:28])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:16][CH:15]=1)[NH2:5]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14505564N-Boc-O-benzyl tyrosine methylamide

Product 1

HCID 14505566HCID 14505566, compound

Procedure

N-tertiarybutoxycarbonyl-O-benzyl-L-tyrosine N-methylamide (3 g) was added to a mixture of TFA and CH2Cl2 (1:1 100 ml) at room temperature. After 15 minutes volatiles were removed in vacuo and the residue was dissolved in water. Neutralisation with solid sodium bicarbonate, extraction into CH2Cl2 and evaporation of the organic extract in vacuo then gave a solid. Co-evaporation of this with ethereal HCl gave O-benzyl-L-tyrosine N-Methylamide hydrochloride.

Workup

  1. customAfter 15 minutes volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionNeutralisation with solid sodium bicarbonate, extraction
  4. custominto CH2Cl2 and evaporation of the
  5. extractionorganic extract in vacuo
  6. customthen gave a solid
  7. customCo-evaporation of this with ethereal HCl

Sources & evidence

ORD record
ord-2704e9fece124dae8249b1f223310ec3
Source dataset
uspto-grants-1986_02
Patent number
US04568666

Reaction notes

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