HCID 86647445, compound → HCID 59569858, compound

HRID 2071186Notes

Reaction equation

HRID 2071186 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:33]=[C:34]([CH:36]([CH3:38])[CH3:37])[CH:35]=1)[CH2:12][NH:13][CH2:14][C@@H:15]([OH:32])[C@@H:16]([NH:24]C(=O)OC(C)(C)C)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1>Cl.CO.[Pd]>[NH2:24][C@@H:16]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@H:15]([OH:32])[CH2:14][NH:13][CH2:12][C:11]1[CH:10]=[C:9]([OH:8])[CH:35]=[C:34]([CH:36]([CH3:37])[CH3:38])[CH:33]=1

Participants

5

Reactant 1

HCID 86647445HCID 86647445, compound

Product 1

HCID 59569858HCID 59569858, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 21.2 mg (0.04 mmol) of tert-butyl (2S,3R)-4-(3-(benzyloxy)-5-isopropylbenzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate and 7.7 mg of 10% Pd/C in 4 mL of 1.25M HCl in MeOH was stirred at r.t. under H2 balloon for 20.5 h. The mixture was filtered through Celite, concentrated, and reconcentrated with toluene 3 times. The amine HCl salt was used for the next reaction without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe amine HCl salt was used for the next reaction without further purification

Sources & evidence

ORD record
ord-4f889a376e5644638e577efb6163a07e
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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