Hydrochloric Acid → HCID 22804687, compound

HRID 2419840Notes

Reaction equation

HRID 2419840 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O=[CH:11][CH2:12][C@@H:13]([C@@H:15]([CH2:17][OH:18])[OH:16])[OH:14].C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>O.O1CCOCC1>[OH:18][CH2:17][C@H:15]([OH:16])[C@@H:13]([OH:14])[CH2:12][CH2:11][N:8]([C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric Acid2×HCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 5003444Sodium cyanoborohydrideHCID 54600052-Deoxyribose, D-

Product 1

HCID 22804687HCID 22804687, compoundYield 55,273.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of benzylamine (2.14 g, 0.02 moles) in water (25 ml) was adjusted to pH5 with 5N hydrochloric acid. 2-Deoxy-D-ribose (1.34 g, 0.01 mole) and sodium cyanoborohydride (0.062 g, 0.01 mole) were added and the solution was allowed to stand for 15 hours at room temperature. The pH of the solution was adjusted to 10 with sodium carbonate and the mixture was washed several times with ethyl acetate. The aqueous solution was cooled to 0° C, and phenyl chloroformate (1.7 g., 0.011 mmoles) in dioxan (15 ml) was added with stirring. After 3 hours at 0° C., the reaction was allowed to warm to room temperature, the pH was adjusted to 7 by the addition of 5N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated under reduced pressure to yield 1,2(S),3(S)-trihydroxy-5-[N-phenoxycarbonyl-N-benzylamino]pentane (2.1 g.) as an oil which slowly solidified on standing. δ (CDCl3 + D2O) 7.2 (10 H, m); 4,5 (2H, s); 3,5 (6 H,m) 1.8 (2H,m). νmax. (film) 3400, 1705, 1600 cm-1.

Workup

  1. washthe mixture was washed several times with ethyl acetate
  2. waitAfter 3 hours at 0° C.
  3. temperatureto warm to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ab26a731a984445eabcbeb62cb7d313d
Source dataset
uspto-grants-1978_08
Patent number
US04107435

Reaction notes

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