Methyl chloroformate → HCID 66553187, compound

HRID 1914506Notes

Reaction equation

HRID 1914506 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([C@H:10]3[C@H:15]([OH:16])[C@@H:14]([OH:17])[C@H:13]([OH:18])[C@@H:12]([CH2:19][OH:20])[O:11]3)=[CH:6][C:5]=2[CH2:21][C:22]2[CH:31]=[CH:30][C:25]3[O:26][CH2:27][CH2:28][O:29][C:24]=3[CH:23]=2)[CH2:3][CH2:2]1.Cl[C:33]([O:35][CH3:36])=[O:34]>N1C(C)=CC(C)=CC=1C.C(Cl)Cl>[CH3:36][O:35][C:33](=[O:34])[O:20][CH2:19][C@@H:12]1[C@@H:13]([OH:18])[C@H:14]([OH:17])[C@@H:15]([OH:16])[C@H:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]3[CH2:3][CH2:2]3)=[C:5]([CH2:21][C:22]3[CH:31]=[CH:30][C:25]4[O:26][CH2:27][CH2:28][O:29][C:24]=4[CH:23]=3)[CH:6]=2)[O:11]1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 52913411(2S,3R,4R,5S,6R)-2-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol2×

Product 1

HCID 66553187HCID 66553187, compoundYield 107.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a stirred solution of (2S,3R,4R,5S,6R)-2-[4-Cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (Intermediate 3, 890 mg, 2.1 mmol) in collidine (7 ml) was added a solution of methyl chloroformate (0.21 ml, 2.5 mmol) in DCM (0.5 ml) at −40° C. After stirring for 1 h at same temperature, it was stirred at room temperature for 1.5 h. Reaction mixture was poured into ice cold 10% HCl solution and extracted with ethyl acetate (2×10 ml). Combined organic layers were washed with brine (10 ml), dried over sodium sulfate, concentrated and purified by silica gel column chromatography to give 1.1 g of carbonic acid (2R,3S,4R,5R,6S)-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester methyl ester as a white solid.

Workup

  1. stirringwas stirred at room temperature for 1.5 h
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. washCombined organic layers were washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e21bfc590fbd4e57910a7098443d758c
Source dataset
uspto-grants-2013_12
Patent number
US08614195B2

Reaction notes

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