tert-Butyl (S,S)-3,3-Dimethyl-3-silabutyl 2-(4-((tert-Butyl)oxycarbonyl)-2-((phenylmethoxy)carbonylamino)butanoylamino)pentane-1,5-dioate → tert-Butyl (S,S)-3,3-Dimethyl-3-silabutyl 2-(2-Amino-4-((tert-butyl)oxycarbonyl)butanoylamino)pentane-1,5-dioate

HRID 9711Notes

Reaction equation

HRID 9711 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C@H:10]([NH:33]C(OCC1C=CC=CC=1)=O)[C:11]([NH:13][C@@H:14]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:25])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)C.[Pd]>[NH2:33][C@@H:10]([CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:11]([NH:13][C@@H:14]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])=[O:25])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:12]

Participants

4

Reactant 1

HCID 86590843tert-Butyl (S,S)-3,3-Dimethyl-3-silabutyl 2-(4-((tert-Butyl)oxycarbonyl)-2-((phenylmethoxy)carbonylamino)butanoylamino)pentane-1,5-dioate

Product 1

HCID 86590842tert-Butyl (S,S)-3,3-Dimethyl-3-silabutyl 2-(2-Amino-4-((tert-butyl)oxycarbonyl)butanoylamino)pentane-1,5-dioateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

The product of step 7G (1.09 g) was dissolved in 2-propanol (75 mL) with 10% palladium on carbon (300 mg) and hydrogenated on a Parr shaker at 45 psi for one hour. The reaction mixture was filtered on a bed of Celite, washed with 2-propanol, and concentrated to yield the product (803 mg, 94%) as a clear oil. LRMS (ES): 489.5 [M+H]+, 977.7 [2M+H]+. 1HNMR (600.1343 MHz, CDCl3): 7.78 (m, 1H), 4.53 (m, 1H), 4.22 (m, 2H), 3.53 (m, 1H), 1.80–2.41 (m, 10H), 1.43 (s, 18H), 1.01 (m, 2H), 0.02 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered on a bed of Celite
  2. washwashed with 2-propanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-99cff4f5665f49449cfff0f103010c1f
Source dataset
uspto-grants-2006_08
Patent number
US07090828B2

Reaction notes

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