Ammonia → HCID 86701301, compound

HRID 1627036Notes

Reaction equation

HRID 1627036 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][O:15][C:14](=[O:26])[C@@H:13]([NH:27]C(=O)OCC2C=CC=CC=2)[CH2:12][O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(C)=O.N.C(O)C>CO.[Pd]>[NH2:27][C@H:13]1[CH2:12][O:11][CH2:10][C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][O:15][C:14]1=[O:26]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 8857Ethyl AcetateHCID 86701302HCID 86701302, compound

Product 1

HCID 86701301HCID 86701301, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

Benzyl (3S,7S,8S)-7,8-bis(benzyloxy)-2-oxo-1,5-dioxonan-3-ylcarbamate (71 mg, 0.140 mmol) was dissolved in MeOH (1 mL) and EtOAc (1 mL) and 2.0 molar (M) ammonia in ethanol (EtOH) (35 μL, 0.070 mmol) and 5% Pd/C (10 mass wt. %) were added. The air was removed by two cycles of evacuating the flask under vacuum and backfilling with H2. The reaction mixture was placed under an atmosphere of H2 (balloon, ˜1 atmosphere) and stirred at room temperature for 2 h. The reaction mixture was filtered through Celite®, and the filtrate was concentrated to afford the title compound as an off-white solid (47 mg, 91%): 1H NMR (400 MHz, CDCl3) δ 7.79-6.92 (m, 10H), 4.79-4.53 (m, 6H), 4.14 (dd, J=11.4, 3.6 Hz, 1H), 3.97 (dd, J=11.4, 7.2 Hz, 1H), 3.87-3.74 (m, 3H), 3.73-3.56 (m, 2H), 3.45 (ddd, J=7.8, 6.0, 1.8 Hz, 1H), 3.25 (dd, J=11.5, 7.9 Hz, 1H); 13C NMR (101 MHz, CDCl3) δ 175.95, 138.09, 138.04, 128.46, 128.40, 128.00, 127.88, 127.85, 127.74, 81.49, 79.46, 75.01, 73.66, 72.75, 71.53, 63.47, 54.33; ESIMS m/z 372.9 ([M+H]+).

Workup

  1. customThe air was removed by two cycles
  2. customof evacuating the flask under vacuum and backfilling with H2
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8828ab3df55c4565ac4941eff89bce67
Source dataset
uspto-grants-2014_07
Patent number
US08785479B2

Reaction notes

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