Boc-Gly-Val-Gly-Ile-Pro-OBzl → Boc-Gly-Val-Gly-Ile-Pro-OH

HRID 1741981Notes

Reaction equation

HRID 1741981 reaction equation
[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:2][C:3]([NH:5][C@H:6]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28]CC1C=CC=CC=1)=[O:27])=[O:23])[C@H:18]([CH2:20][CH3:21])[CH3:19])=[O:15])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]>C(O)(=O)C.[Pd]>[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])[CH2:2][C:3]([NH:5][C@H:6]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])[C@H:18]([CH2:20][CH3:21])[CH3:19])=[O:15])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]

Participants

4

Reactant 1

HCID 131715771Boc-Gly-Val-Gly-Ile-Pro-OBzl

Product 1

HCID 131716314Boc-Gly-Val-Gly-Ile-Pro-OHYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

III (7.8 g, 0.0123 mole) was taken in acetic acid (80 ml) and hydrogenated in the presence of 10% Pd-C (1 g) at 40 psi. After filtering the catalyst with the aid of celite, the solvent was removed under reduced pressure, triturated with ether, filtered, washed with ether then pet. ether and dried to obtain 6.5 g of the product (yield: 97.3%), m.p. shrinks at 127° C. and decomp. at 145° C. Rf3, 0.24; Rf4, 0.11. Anal. Calcd. for C25H43N5O10.1/2H2O: C 54.52, H 8.05, N 12.7%. Found: C 54.32, H 8.02, N 12.59%.

Workup

  1. filtrationAfter filtering the catalyst with the aid of celite
  2. customthe solvent was removed under reduced pressure
  3. customtriturated with ether
  4. filtrationfiltered
  5. washwashed with ether
  6. dry with materialpet. ether and dried

Sources & evidence

ORD record
ord-578a159beee341d2b58485cb5c4523f5
Source dataset
uspto-grants-1994_08
Patent number
US05336256

Reaction notes

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