HCID 86702755, compound → HCID 60162765, compound

HRID 526263Notes

Reaction equation

HRID 526263 reaction equation
C(OC([NH:11][C@H:12]([C@@H:33]([NH:41][C:42](=[O:63])[C@@H:43]([NH:48][C:49](=[O:62])[C@@H:50]([NH:55][C:56](=[O:61])[CH2:57][CH:58]([CH3:60])[CH3:59])[CH2:51][CH:52]([CH3:54])[CH3:53])[C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:13][C:14]([NH:16][C@@H:17]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[C:18]([NH:20][C@@H:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])=[O:19])=[O:15])=O)C1C=CC=CC=1>C1COCC1.[Pd]>[NH2:11][C@H:12]([C@@H:33]([NH:41][C:42](=[O:63])[C@@H:43]([NH:48][C:49](=[O:62])[C@@H:50]([NH:55][C:56](=[O:61])[CH2:57][CH:58]([CH3:60])[CH3:59])[CH2:51][CH:52]([CH3:53])[CH3:54])[C:44]([CH3:45])([CH3:47])[CH3:46])[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH2:13][C:14]([NH:16][C@@H:17]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[C:18]([NH:20][C@@H:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])=[O:19])=[O:15]

Participants

4

Reactant 1

HCID 86702755HCID 86702755, compound

Product 1

HCID 60162765HCID 60162765, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

300 mg of methyl (S)-2-[(2S,3S)-2-((3S,4S)-3-benzyloxycarbonylamino-4-{(S)-3,3-dimethyl-2-[(S)-4-methyl-2-(3-methylbutyrylamino)pentanoylamino]-butyrylamino}-5-phenylpentanoylamino)-3-methylpentanoylamino]-3-methylbutyrate were hydrogenated in a suitable vessel in the presence of 300 mg of Pd/C (5% of Pd) in 30 ml of THF at RT at atmospheric pressure until the starting material had reacted completely (overnight). The solvent was removed in vacuo, and the residue was triturated with MTBE and filtered off with suction. Purification by preparative HPLC (Chromolith®prep, RP18e, 100-25; gradient water:acetonitrile 1-60% in 12 min) and subsequent lyophilisation gave 89 mg of methyl (S)-2-[(2S,3S)-2-((3S,4S)-3-amino-4-{(S)-3,3-dimethyl-2-[(S)-4-methyl-2-(3-methylbutyrylamino)pentanoylamino]butyrylamino}-5-phenylpentanoylamino)-3-methylpentanoylamino]-3-methylbutyrate as a white powder (yield 31%). MS-FAB (M+H+)=746.1 Rf (polar method): 2.02 min.

Workup

  1. customhad reacted completely (overnight)
  2. customThe solvent was removed in vacuo
  3. customthe residue was triturated with MTBE
  4. filtrationfiltered off with suction
  5. customPurification by preparative HPLC (Chromolith®prep, RP18e, 100-25; gradient water:acetonitrile 1-60% in 12 min) and subsequent lyophilisation

Sources & evidence

ORD record
ord-48434dba3ef5452f92f5ce7a52f791ca
Source dataset
uspto-grants-2016_05
Patent number
US09345742B2

Reaction notes

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