Acetic Acid → HCID 67318604, compound

HRID 1985440Notes

Reaction equation

HRID 1985440 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:27][C:19]3[C:20]4[CH:21]=[N:22][NH:23][C:24]=4[CH:25]=[CH:26][C:18]=3[CH2:17][C@@H:16]([NH:28]C(OCC3C=CC=CC=3)=O)[C:15]2=[O:39])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40]([OH:43])(=[O:42])[CH3:41].[H][H]>[Pd].CO>[C:40]([OH:43])(=[O:42])[CH3:41].[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:27][C:19]3[C:20]4[CH:21]=[N:22][NH:23][C:24]=4[CH:25]=[CH:26][C:18]=3[CH2:17][C@@H:16]([NH2:28])[C:15]2=[O:39])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 59731964HCID 59731964, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67318604HCID 67318604, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A catalytic amount of 10% palladium on carbon was added to a solution of 4-(7-(R)-Benzyloxycarbonylamino-8-oxo-6,7,8,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-9-yl)-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.37 mmol) and acetic acid (100 μL, 1.7 mmol) in methanol (10 mL). Reaction vessel was placed on a Parr apparatus and charged with 30 psi of hydrogen gas. Mixture was allowed to shake at room temperature for 3 hours. Mixture was filtered. Filtrate was concentrated in vacuo. Crude compound was obtained as a dark oil in quantitative yield. Material was carried forward without further purification. 1H NMR (300 MHz, CDCl3): δ=8.06 (s, 1H), 7.36 (d, J=8.8, 1H), 7.12 (d, J=8.8, 1H), 4.92 (d, J=17.6, 1H), 4.67 (m, 1H), 4.49 (d, J=17.2, 1H), 4.26 (m, 1H), 3.98 (m, 2H), 3.05 (m, 1H), 2.83 (m, 2H), 2.64 (m, 1H), 1.89 (m, 1H), 1.73 (m, 1H), 1.45 (d, J=2.9, 9H), 1.25 (m, 2H). MS m/e (M−C4H8+H)+=344.2.

Workup

  1. customReaction vessel
  2. filtrationMixture was filtered
  3. concentrationFiltrate was concentrated in vacuo
  4. customCrude compound was obtained as a dark oil in quantitative yield
  5. customMaterial was carried forward without further purification

Sources & evidence

ORD record
ord-c950b1da6f9c4d68997d2cb5e781929b
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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