Hydrochloric Acid → HCID 66951003, compound

HRID 1171242Notes

Reaction equation

HRID 1171242 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-bae924a8d86d4429a5b235fc5fb1e93a
Source dataset
uspto-grants-2010_11
Patent number
US07829592B2

Reaction notes

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