Ammonia → HCID 21825595, compound

HRID 917825Notes

Reaction equation

HRID 917825 reaction equation
[NH3:1].C[O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C@@H:11]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C3C=CC=CC=3)[C@@H:22]([O:23]C(=O)C3C=CC=CC=3)[C@H:12]2[O:13]C(=O)C2C=CC=CC=2)[N:10]=1)=O>CO>[C@@H:11]1([N:9]2[N:10]=[C:6]([C:4]([NH2:1])=[O:3])[CH:7]=[N:8]2)[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([OH:23])[C@H:12]1[OH:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21825581HCID 21825581, compound

Product 1

HCID 21825595HCID 21825595, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol saturated with ammonia at 0° (ca 150 ml) was added to 5.71 g (0.010 mol) of 1 in a pressure bottle and kept at room temperature for 4 days. After removal of the solvent, water (30 ml) was added and the mixture was extracted with ether (six 20 ml portions). The solvent was removed and the compound crystallized from ethanol to give 2.25 g (92%) of 4: m.p. 150°-151°; [α]D25 -59.4° (c 1.00, water); nmr (DMSO-d6) δ 5.97 (d, 1, J1',2' 4.0 Hz, 1'--H).

Workup

  1. customAfter removal of the solvent, water (30 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ether (six 20 ml portions)
  4. customThe solvent was removed
  5. customthe compound crystallized from ethanol

Sources & evidence

ORD record
ord-10aaf15cb2404bd0b311c62ebdf637fd
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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