Hydrochloric Acid → HCID 70907144, compound

HRID 1914505Notes

Reaction equation

HRID 1914505 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]3[CH:13]=[C:14]([C@@H:20]4[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:41])[C@H:29]([NH:33]C(OC(C)(C)C)=O)[CH:30]([CH3:32])[CH3:31])[C@@H:23]([OH:42])[C@H:22]([OH:43])[C@H:21]4[OH:44])[CH:15]=[CH:16][C:17]=3[CH2:18][CH3:19])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.Cl>CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]3[CH:13]=[C:14]([C@@H:20]4[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:41])[C@H:29]([NH2:33])[CH:30]([CH3:32])[CH3:31])[C@@H:23]([OH:42])[C@H:22]([OH:43])[C@H:21]4[OH:44])[CH:15]=[CH:16][C:17]=3[CH2:18][CH3:19])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70913586HCID 70913586, compound

Product 1

HCID 70907144HCID 70907144, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (R)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (2.8 g, 4.6 mmol) in methanol (30 ml) was added 3 N methanolic HCl (30 ml) at room temperature. After refluxing for 2 h, volatiles were evaporated under reduced pressure. The resulting residue was taken in ethyl acetate (50 ml) and washed with aqueous saturated sodium bicarbonate solution (15 ml), brine (15 ml), dried over sodium sulfate, concentrated, and purified by preparative HPLC to give 410 mg of (R)-2-Amino-3-methyl-butyric acid (2R,3S,4R,5R,6S)-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester as a white solid.

Workup

  1. temperatureAfter refluxing for 2 h
  2. customvolatiles were evaporated under reduced pressure
  3. washwashed with aqueous saturated sodium bicarbonate solution (15 ml), brine (15 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-91a6ae681c85440785d42d687fcb7165
Source dataset
uspto-grants-2013_12
Patent number
US08614195B2

Reaction notes

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