BocPro-DTrp-PheOBz → BocPro-DTrp-PheOH

HRID 2418577Notes

Reaction equation

HRID 2418577 reaction equation
[N:1]1([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:41][CH2:40][CH2:39][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([O:30]C(C1C=CC=CC=1)=O)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]>[Pd].C(O)C.CO>[N:1]1([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:41][CH2:40][CH2:39][C@H:2]1[C:3]([NH:5][C@@H:6]([C:17]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 1

HCID 131713759BocPro-DTrp-PheOBz

Product 1

HCID 131713758BocPro-DTrp-PheOHYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

A mixture of palladium on carbon (10%, 4.0 g.) in ethanol (20 ml.) was added to a solution of BocPro-DTrp-PheOBz (70.44 mmole.) in methanol (100 ml.). The mixture was diluted to 200 ml. with methanol, hydrogenated under pressure for three hours and filtered. The filtrate was stripped of volatiles. After unsuccessful attempts to crystallize the residue from ether-hexane and methanol-water it was twice dissolved in, and stripped of, chloroform and dried under high vacuum, affording BocPro-DTrp-PheOH in 95% yield as a foam (36.6 g.).

Workup

  1. additionThe mixture was diluted to 200 ml
  2. filtrationfiltered
  3. customAfter unsuccessful attempts to crystallize the residue from ether-hexane and methanol-water it
  4. dissolutionwas twice dissolved in, and
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-f37fd5b1b9174337b55480a339a34a69
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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