Methanol → HCID 14209965, compound

HRID 1031444Notes

Reaction equation

HRID 1031444 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:14][C:8]3=[CH:7][C:6]=2[C:5](=[O:21])[NH:4][C:3]1=[O:22].O1CCOCC1.CO.[BH4-].[Na+]>O>[CH3:1][C:2]1([CH3:23])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)=[N:14][C:8]3=[CH:7][C:6]=2[C:5](=[O:21])[NH:4][CH:3]1[OH:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 4311764Sodium borohydrideHCID 14209964HCID 14209964, compound

Product 1

HCID 14209965HCID 14209965, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

5 g. (17 mmole) of the compound obtained in Example 8 were suspended in 250 ml. dioxan, 250 ml. methanol and 25 ml. water. While cooling with water, sodium borohydride was added thereto in 0.5 g. portions. After each addition, the course of the reaction is monitored chromatographically. When the substance had just gone into solution (conversion 70% of theory), the reaction is discontinued. The product is precipitated by the addition of 1 litre of water and evaporated to give 3.8 g. (76% of theory) of the title compound; m.p. 260 -268° C.

Workup

  1. additionwas added
  2. additionAfter each addition
  3. customThe product is precipitated by the addition of 1 litre of water
  4. customevaporated
  5. customto give 3.8 g

Sources & evidence

ORD record
ord-5259e07d125a4b829cbbf112590da348
Source dataset
uspto-grants-1990_09
Patent number
US04954498

Reaction notes

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