Hydrochloric Acid → HCID 57086179, compound

HRID 2294696Notes

Reaction equation

HRID 2294696 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:15]C(=O)OC(C)(C)C)[C@@H:9]([OH:14])[CH:10]([OH:13])[CH2:11][OH:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.Cl>C1(C)C=CC=CC=1>[NH2:15][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@@H:9]([OH:14])[CH:10]([OH:13])[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86751636HCID 86751636, compound

Product 1

HCID 57086179HCID 57086179, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 270 mg of tert-butyl [(1S,2R,3RS)-1-(cyclohexylmethyl)-2,3,4-trihydroxybutyl]carbamate, 15 ml of methanol and 10 ml of 2N hydrochloric acid is heated to 50° overnight. Subsequently, the reaction solution is evaporated to dryness under reduced pressure, the residue obtained is taken up twice in toluene and evaporated to dryness under reduced pressure each time. The crude (2RS,3R,4S)-4-amino-5-cyclohexyl-1,2,3-pentanetriol obtained is used in the next step without further purification; MS: 218 (M+H)+.

Workup

  1. customSubsequently, the reaction solution is evaporated to dryness under reduced pressure
  2. customthe residue obtained
  3. customevaporated to dryness under reduced pressure each time

Sources & evidence

ORD record
ord-47cfd517198d44efac53994043d73a10
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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