Methyl chloroformate → HCID 10292533, compound

HRID 2065992Notes

Reaction equation

Cl.[CH:2]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:16]1[N:17]=[C:18]([CH2:21][NH2:22])[S:19][CH:20]=1.C(N(CC)CC)C.[CH3:30][O:31][C:32](Cl)=[O:33]>O1CCOCC1>[CH:2]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:16]1[N:17]=[C:18]([CH2:21][NH:22][C:32](=[O:33])[O:31][CH3:30])[S:19][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The compound of Example 362 (0.622 g; 2.0 mmol) is dissolved in dioxane (100 ml) cooled down to 0° C. Triethylamine is added, then, dropwise, methylchloroformate (2.5 mmol). The reaction medium is then stirred for 3 hours at ambient temperature before being poured into ice-cold water and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum. The expected product is purified on a silica column (eluent: 10% acetone in dichloromethane). The pure fractions are combined and the solvents are evaporated off in order to produce an off-white solid with a yield of 46.0%. Melting point: 151-153° C.

Workup

additionbefore being poured into ice-cold water
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under vacuum
customThe expected product is purified on a silica column (eluent: 10% acetone in dichloromethane)
customthe solvents are evaporated off in order
customto produce an off-white solid with a yield of 46.0%

Sources & evidence

ORD record: ord-0fd50c88e6254c0cb1a383a35ae7642a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288560B2

Reaction notes

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