Methyl chloroformate → Methyl-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate

HRID 335498Notes

Reaction equation

HRID 335498 reaction equation
C(N[C:4]1[S:5][C@H:6]2[O:12][C@H:11]([CH2:13][OH:14])[C@@H:10]([OH:15])[C@H:9]([OH:16])[C@H:7]2[N:8]=1)C.[CH2:17]([N:19](C(C)C)C(C)C)[CH3:18].Cl[C:27]([O:29][CH3:30])=[O:28].CO.C(Cl)Cl>C1COCC1>[CH3:30][O:29][C:27](=[O:28])[NH:19][CH2:17][CH2:18][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([CH2:13][OH:14])[C@@H:10]([OH:15])[C@H:9]([OH:16])[C@H:7]2[N:8]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 21226129Dichloromethane methanolHCID 24808478Thiamet G, >=98% (HPLC)

Product 1

HCID 131732010Methyl-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (100.00 mg; 0.40 mmol; 1.00 eq.) in dry THF (12 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.09 ml; 0.52 mmol; 1.30 eq.). The mixture was cooled to 0° C. then methyl chloroformate (0.05 ml, 0.60 mmol, 1.50 eq.) was added dropwise. The reaction was stirred at room temperature for 2 h. The desired product was isolated by flash chromatography (KPNH column, 10 to 100% MeOH/DCM) to afford methyl [(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate (19.6 mg, 16%) as a white solid (once lyophilized).

Sources & evidence

ORD record
ord-525bbf308585424ab996bea2b746ad98
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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