Hydrochloric Acid → HCID 66951003, compound

HRID 2190220Notes

Reaction equation

HRID 2190220 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:8]=[C:9]([CH2:19][C@H:20]([NH:31]C(OC(C)(C)C)=O)[C:21]([O:23][C@H:24]([CH3:30])[CH2:25][O:26][C:27](=[O:29])[CH3:28])=[O:22])[CH:10]=[CH:11][C:12]=1[O:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[ClH:39]>O1CCOCC1>[ClH:39].[NH2:31][C@@H:20]([CH2:19][C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([O:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:8]=1)[C:21]([O:23][C@H:24]([CH3:30])[CH2:25][O:26][C:27](=[O:29])[CH3:28])=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66951785HCID 66951785, compound

Product 1

HCID 66951003HCID 66951003, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1R)-2-Acetyloxy-1-methylethyl (2S)-3-[3,4-bis(ethoxycarbonyloxy)phenyl]-2-[(tert-butoxy)carbonylamino]propanoate (20) (11.5 g, 21.2 mmol) was dissolved in 60 mL of 4M HCl in dioxane. The resulting mixture was stirred at room temperature for 60 min. Solvent removal under reduced pressure gave 10.1 g (100% yield) of the title compound (14) as a colorless oil. 1H NMR (400 MHz, CD3OD): δ 1.21 (d, J=6.4 Hz, 3H), 1.35 (t, J=7.2 Hz, 3H), 1.36 (t, J=7.2 Hz, 3H), 2.04 (s, 3H), 3.26 (d, J=7.2 Hz, 2H), 4.05 (dd, J=8.8, 6.4 Hz, 1H), 4.23 (dd, J=12.4, 3.2 Hz, 1H), 4.28 (q, J=6.8 Hz, 2H), 4.30 (q, J=6.8 Hz, 2H), 4.37 (t, J=7.2 Hz, 1H), 5.19 (m, 1H), 7.27 (dd, J=8.0, 2.0 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H). MS (ESI) m/z 442.1 (M+H)+.

Workup

  1. customSolvent removal under reduced pressure

Sources & evidence

ORD record
ord-f4faa54926294e9ab3fcf2ec87e8dbb6
Source dataset
uspto-grants-2012_12
Patent number
US08324273B2

Reaction notes

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