Methanol → HCID 178471596, compound

HRID 1489182Notes

Reaction equation

HRID 1489182 reaction equation
[NH2:1][C@H:2]1[C@@:7]([OH:9])([CH3:8])[C:6]([CH3:11])([CH3:10])[O:5][C:4]2[CH:12]=[CH:13][C:14]([C:16]3[N:20]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:19]=[N:18][N:17]=3)=[CH:15][C:3]1=2.[CH3:29][S:30][C:31](SC)=[N:32][C:33]#[N:34].N1C=CC=CC=1.CO>ClCCl>[C:33]([N:32]=[C:31]([S:30][CH3:29])[NH:1][C@H:2]1[C@@:7]([OH:9])([CH3:8])[C:6]([CH3:10])([CH3:11])[O:5][C:4]2[CH:12]=[CH:13][C:14]([C:16]3[N:20]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:19]=[N:18][N:17]=3)=[CH:15][C:3]1=2)#[N:34]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 57041522HCID 57041522, compound

Product 1

HCID 178471596HCID 178471596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture containing (3S,4R)-4-amino-3,4-dihydro-6-(1-[3-ethoxycarbonylprop-1-yl]-1H-tetrazol-5-yl)-3-hydroxy-2,2,3-trimethyl-2H-benzo[b]pyran (see Preparation 55) (1.2 g), dimethyl N-cyanodithioiminocarbonate (0.7 g) and pyridine (10 ml) was heated at 75° C. for 18 hours then concentrated in vacuo to give a gum which was stirred in dichloromethane containing methanol (2.5%) (20 ml). The resulting solid was filtered off and dried in vacuo to give the title compound, 0.85 g, m.p. 225°-227° C. Found: C,54.13; H,5.91; N,19.81; C22H29N7O4S requires: C,54.20; H,6.00; N,20.11%.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto give a gum which
  3. filtrationThe resulting solid was filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-64b080a55a7344df8d79280ef522ef71
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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