Hydrochloric Acid → HCID 20334542, compound

HRID 1111786Notes

Reaction equation

HRID 1111786 reaction equation
[O:1]=[C:2]([CH2:26][O:27]C(=O)C)[CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([OH:11])=[O:10].[BH4-].[Na+].C([O-])([O-])=O.[Na+].[Na+].Cl>C(O)C.CO.O>[OH:1][CH:2]([CH2:26][OH:27])[CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([OH:11])=[O:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 20334544HCID 20334544, compound

Product 1

HCID 20334542HCID 20334542, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A slurry of 3-(γ-oxo-δ-acetoxybutylamino)-4-phenoxy-5-sulfamylbenzoic acid (1.5 g) in ethanol (10 ml) was treated with sodium borohydride (0.5 g) and the mixture was heated on the steam bath with occasional swirling until a clear solution had formed. Water and aq. Na2CO3 were added and heating on the steam bath continued for about 10 min. The solution was cooled and carefully acidified with 3N aqueous HCl. Some methanol was added and the solution was concentrated to ca. 20 ml under reduced pressure. Partial neutralization with aq. Na2CO3 caused the product to separate as a gum, which soon solidified. The product was filtered, washed with water, and air-dried to give 1.1 g (80%) of 3-(γ, δ-dihydroxybutylamino)-4-phenoxy-5-sulfamylbenzoic acid as a colorless powder. A sample was recrystallized from methanol/water to give needles with mp 235°-238°; ir (Nujol) 3500, 3400, 2700 (broad) 1710, 1625, 1600, and 1525 cm-1 ; nmr (d6 -DMSO) 1.5 (m, broad, 2H) 3.0-3.5 (m, broad, 5H), 5.13 (s, broad, NH), 6.7-7.3 (m, C6H5), 7.17 (s, SO2NH2), 7.31 (d, J=2, CH), and 7.66 ppm, d, J=2, CH); mass spectrum m/e 378, 396 (M+).

Workup

  1. temperaturethe mixture was heated on the steam bath
  2. customhad formed
  3. temperatureheating on the steam bath
  4. temperatureThe solution was cooled
  5. concentrationthe solution was concentrated to ca. 20 ml under reduced pressure
  6. customto separate as a gum, which
  7. filtrationThe product was filtered
  8. washwashed with water
  9. customair-dried

Sources & evidence

ORD record
ord-28bdf0b39fb14cb5afc993cb00a8236a
Source dataset
uspto-grants-1978_10
Patent number
US04118587

Reaction notes

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