Hydrochloric Acid → HCID 86705521, compound

HRID 2279522Notes

Reaction equation

HRID 2279522 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@H:17]2[CH2:21][O:20]C3(CCCCC3)[O:18]2)[NH:10][S@](C(C)(C)C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.CC(O)C.O1CCOCC1>O.C(Cl)Cl>[ClH:1].[NH2:10][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[C@H:17]([OH:18])[CH2:21][OH:20]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3776IsopropanolHCID 312751,4-DioxaneHCID 86705520HCID 86705520, compound

Product 1

HCID 86705521HCID 86705521, compoundYield 187.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 250 (1.8 g, 4.3 mmol) and DCM (5 mL) was added a solution of HCl in IPA (7.1 mL, 43 mmol) and the reaction was stirred for 1 h. The reaction concentrated to dryness and 4M HCl in dioxane (5 eq) and H2O (1 mL) was added to cleave the cyclohexyl ketal. The reaction was stirred for 1 h and then concentrated to dryness to afford 1.1 g (94%) of (2S,3S)-3-amino-3-(3,4-dichlorophenyl)propane-1,2-diol hydrochloride (252).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for 1 h
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0768dcdce7484bd69239dd33d5e90d2c
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…