Acetic Acid → HCID 178484351, compound

HRID 2403988Notes

Reaction equation

HRID 2403988 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:33](=[O:49])[NH:34][CH2:35][CH2:36][N:37](C(OCC1C=CC=CC=1)=O)[CH3:38])[CH2:9][CH2:10][CH2:11][NH:12]/[C:13](/[NH2:32])=[N:14]/[S:15]([C:18]1[C:19]([CH3:31])=[C:20]([CH3:30])[C:21]2[O:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]=2[C:28]=1[CH3:29])(=[O:17])=[O:16])(C)(C)C.CC(O)=O>CO.O.[Pd]>[CH3:38][NH:37][CH2:36][CH2:35][NH:34][C:33](=[O:49])[C@@H:8]([NH2:7])[CH2:9][CH2:10][CH2:11][NH:12]/[C:13](/[NH2:32])=[N:14]/[S:15]([C:18]1[C:19]([CH3:31])=[C:20]([CH3:30])[C:21]2[O:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]=2[C:28]=1[CH3:29])(=[O:17])=[O:16]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 178427591{(S)-4-({amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-1-[2-(benzyloxycarbonyl-methyl-amino)-ethyl carbamoyl]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 178484351HCID 178484351, compoundYield 55.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Compound D (4.14 g, 5.77 mmol) and AcOH (330 μl, 5.77 mmol) was dissolved in methanol (40 ml) followed by the addition of Pd/C (5% wt, 880 mg) suspension in water (5 ml). The reaction mixture was subjected to hydrogenation (Parr apparatus, 75 psi) at room temperature for 2.5 h. The catalyst was filtered over a pad of Celite on sintered glass funnel and washed with methanol. Filtrate was evaporated in vacuo to provide compound E (1.96 g, 3.2 mmol) as yellowish amorphous solid. LC-MS [M+H] 483.2 (C22H38N6O4S+H, calc: 483.2).

Workup

  1. filtrationThe catalyst was filtered over a pad of Celite on sintered glass funnel
  2. washwashed with methanol
  3. customFiltrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ea76c694321043bcb70e63e4d309d61f
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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