Hydrochloric Acid → HCID 25066682, compound

HRID 2190213Notes

Reaction equation

HRID 2190213 reaction equation
[CH:1]([O:4][C:5]([O:7][C:8]1[CH:9]=[C:10]([CH2:21][C@H:22]([NH:38]C(OC(C)(C)C)=O)[C:23]([O:25][C@H:26]([CH3:37])[CH2:27][O:28][C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[O:24])[CH:11]=[CH:12][C:13]=1[O:14][C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[O:6])([CH3:3])[CH3:2].[ClH:46]>O1CCOCC1>[ClH:46].[NH2:38][C@@H:22]([CH2:21][C:10]1[CH:11]=[CH:12][C:13]([O:14][C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[C:8]([O:7][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH:9]=1)[C:23]([O:25][C@H:26]([CH3:37])[CH2:27][O:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30])=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621597HCID 86621597, compound

Product 1

HCID 25066682HCID 25066682, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-3-[3,4-bis(isopropoxycarbonyloxy)phenyl]-2-[(tert-butoxy)carbonylamino]propanoate (9) (1.06 g, 1.63 mmol) was dissolved in 10 mL of 4M HCl in dioxane. The reaction mixture was stirred at room temperature for 60 min. Dioxane was evaporated completely under reduced pressure. The resulting white solid was dissolved in water (15 mL) and washed with methyl tert-butyl ether. The aqueous phase was collected and mixed with acetonitrile (10 mL). Lyophilization gave the title compound (8) (0.926 g, 100% yield) as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.30 (3H, d, J=6.4 Hz), 1.35 (12H, d, J=6.4 Hz), 3.16 (1H, dd, J=14.4, 6.8 Hz), 3.23 (1H, dd, J=14.4, 6.4 Hz), 4.28 (1H, t, J=6.8 Hz), 4.31 (1H, dd, J=12.4, 6.4 Hz), 4.48 (1H, dd, J=12, 2.8 Hz), 5.33 (1H, m), 7.19 (1H, dd, J=8.2 Hz), 7.24 (1H, d, J=2 Hz), 7.25 (1H, d, J=8 Hz), 7.48 (2H, t, J=7.2 Hz), 7.60 (1H, t, J=7.2 Hz), 8.00 (2H, d, J=7.6 Hz). MS (ESI) m/z 532.21 (M+H)+.

Workup

  1. customDioxane was evaporated completely under reduced pressure
  2. dissolutionThe resulting white solid was dissolved in water (15 mL)
  3. washwashed with methyl tert-butyl ether
  4. customThe aqueous phase was collected
  5. additionmixed with acetonitrile (10 mL)

Sources & evidence

ORD record
ord-112ea1469ca6448aa81dada5dc1f125a
Source dataset
uspto-grants-2012_12
Patent number
US08324273B2

Reaction notes

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