Diethyl Ether → HCID 178427505, compound

HRID 1417888Notes

Reaction equation

HRID 1417888 reaction equation
[NH:1]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@@H:2]([C:14]([N:16]([CH3:49])[C@H:17]([C:35]([NH:37][CH2:38][C:39]([O:41]CC1C=CC=CC=1)=[O:40])=[O:36])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:34])[NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].C(OCC)C>CO>[NH:1]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@@H:2]([C:14]([N:16]([CH3:49])[C@H:17]([C:35]([NH:37][CH2:38][C:39]([OH:41])=[O:40])=[O:36])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:34])[NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:25])=[O:26])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]([F:12])([F:11])[F:13])=[O:9]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 178427502HCID 178427502, compound

Product 1

HCID 178427505HCID 178427505, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Boc-D-Lys(Tfa)-NMeArg(Tos)-Gly-OBzl (11.00 g, 13.5 mmol) in methanol (200 ml) was placed in a Parr shaker bottle, purged with N2 for 10 minutes, and treated with 10% palladium on carbon catalyst (10% Pd/C, 3.6 g). The shaker bottle was further purged with 7 pressurization-evacuation cycles, repressurized, and allowed to shake 90 minutes, during which time the calculated amount of hydrogen was consumed. The catalyst was removed by filtration through a bed of Celite and the filtrate was concentrated under reduced pressure yielding a solid. Trituration with refluxing ethyl ether (75 ml) gave pure product (9.18 g, 94%) as a colorless solid. DCI-MS: [M+H]=724.

Workup

  1. custompurged with N2 for 10 minutes
  2. additiontreated with 10% palladium on carbon catalyst (10% Pd/C, 3.6 g)
  3. customThe shaker bottle was further purged with 7 pressurization-evacuation cycles
  4. customthe calculated amount of hydrogen was consumed
  5. customThe catalyst was removed by filtration through a bed of Celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customyielding a solid

Sources & evidence

ORD record
ord-524f459873ec4775aa789e9b57401de2
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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