Trp(Tos)-OBzl → H-Trp(Tos)-OH

HRID 1649340Notes

Reaction equation

HRID 1649340 reaction equation
[NH2:1][C@H:2]([C:23]([O:25]CC1C=CC=CC=1)=[O:24])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:5]=1>C(O)(=O)C>[NH2:1][C@H:2]([C:23]([OH:25])=[O:24])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:14])=[O:15])[CH:5]=1

Participants

3

Reactant 1

HCID 131713224Trp(Tos)-OBzl

Product 1

HCID 53912663H-Trp(Tos)-OH

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 80% acetic acid (20 ml) was suspended Tr-Trp(Tos)-OBzl (1.3 g, 1.88 mM) and the mixture was stirred at room temperature for one hour, whereby the material was dissolved. The precipitated triphenylmethanol was filtered off and the filtrate was subjected to catalytic reduction for 4 hours in the presence of palladium black at room temperature. The catalyst was filtered off and the acetic acid was distilled off. The residue was recrystallized from water to give H-Trp(Tos)-OH. Yield 585 mg (86.9%); m.p. 227° C. (decomp.); [α]D21 -29.2° (c=0.5, acetic acid).

Workup

  1. dissolutionwhereby the material was dissolved
  2. filtrationThe precipitated triphenylmethanol was filtered off
  3. waitthe filtrate was subjected to catalytic reduction for 4 hours in the presence of palladium black at room temperature
  4. filtrationThe catalyst was filtered off
  5. distillationthe acetic acid was distilled off
  6. customThe residue was recrystallized from water

Sources & evidence

ORD record
ord-4994a4c1b6a3460db48d89c520dd4895
Source dataset
uspto-grants-1983_11
Patent number
US04416820

Reaction notes

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