Ammonia → HCID 66551358, compound

HRID 1422544Notes

Reaction equation

HRID 1422544 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([CH2:14][O:15]C(=O)C)[O:12][C@H:11]2[C@H:7]([N:8]=[C:9]([NH:19][CH2:20][CH2:21][CH:22]3[CH2:24][CH2:23]3)[S:10]2)[C@H:6]1[O:25]C(=O)C)(=O)C.N>CO>[CH:22]1([CH2:21][CH2:20][NH:19][C:9]2[S:10][C@H:11]3[O:12][C@H:13]([CH2:14][OH:15])[C@@H:5]([OH:4])[C@H:6]([OH:25])[C@H:7]3[N:8]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66548967HCID 66548967, compound

Product 1

HCID 66551358HCID 66551358, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-cyclopropylethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (15 g, 36 mmol) in MeOH (400 mL) was bubbled with NH3(g) for 2 h. After stirred overnight at room temperature, the reaction mixture was condensed to give a residue, which was washed with hot ethyl acetate to provide the title compound as a white solid (9 g, 86%). (ES, m/z): [M+H]+289.0; 1H NMR (300 MHz, CDCl3) δ 6.18-6.20 (d, J=6.3 Hz, 1H), 4.10-4.12 (m, 1H), 3.93-3.97 (m, 1H), 3.70-3.75 (m, 1H), 3.47-3.62 (m, 3H), 3.20-3.25 (m, 2H), 1.32-1.38 (m, 2H), 0.61-0.65 (m, 1H), 0.36-0.37 (m, 2H), 0.08-0.12 (m, 2H).

Workup

  1. customcondensed
  2. customto give a residue, which
  3. washwas washed with hot ethyl acetate

Sources & evidence

ORD record
ord-a8c5f07c42cf4306865902325e076bb7
Source dataset
uspto-grants-2015_01
Patent number
US08927507B2

Reaction notes

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