Acetic Acid → HCID 178490621, compound

HRID 366034Notes

Reaction equation

HRID 366034 reaction equation
C([NH:11][C:12](=[N:47]C(OCC1C=CC=CC=1)=O)[NH:13][CH2:14][CH2:15][CH2:16][C@@H:17]([C:34]([NH:36][C@@H:37]([C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)[CH3:38])=[O:35])[NH:18][C:19](=[O:33])[CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(OCC1C=CC=CC=1)=O.CC(O)=O.[ClH:62]>[Pd].CO>[ClH:62].[C:21]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:19]([NH:18][C@H:17]([C:34]([NH:36][C@@H:37]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[CH3:38])=[O:35])[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[NH:11])[NH2:47])=[O:33])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 178490619HCID 178490619, compound

Product 1

HCID 178490621HCID 178490621, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared according to the method described in Example 1(g) above from (R)-Nω,Nω '-bis(Cbz)-N2 -(diphenylacetyl)-(S)-N-[1-(4-methoxyphenyl)ethyl]-arginine amide (2.8 g; from step (e) above), 10% Pd/C (1.5 g), and, instead of HOAc, MeOH (225 mL) and concentrated HCl (21 mL) under hydrogen, 18 hours reaction time, which gave the crude product (1.8 g). Crystallization from MeOH:diethyl ether then from isopropanol:diethyl ether afforded the sub-title compound as a white solid (0.75 g).

Workup

  1. customPrepared
  2. customgave the crude product (1.8 g)
  3. customCrystallization from MeOH

Sources & evidence

ORD record
ord-bb01544f2a91439381ac2a9b911ce392
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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