Hydrochloric Acid → HCID 22841630, compound

HRID 1460412Notes

Reaction equation

HRID 1460412 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[CH2:10](N(CC)CC)C.CO[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.Cl.[OH2:28]>O=O>[CH3:10][O:28][S:6][C:3]([CH3:5])([CH3:4])[C@H:2]([C:7]([OH:9])=[O:8])[NH:1][CH2:23][C:22]1[CH:25]=[CH:26][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 5852PenicillamineHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 22841630HCID 22841630, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent2×

Procedure

To a suspension of D-Penicillamine (99.7 g; 668 mmol) in a mixture of oxygen-free isopropanol (590 ml) and oxygen-free water (470 ml), triethylamine (187 ml; 1330 mmol) was added under cooling. To the resultant suspension, p-methoxybenzyl chloride (136 g; 868 mmol) was dropwise added, and the mixture was stirred at room temperature overnight. The reaction mixture was combined with water (1000 ml), adjusted to pH 3 with 3N hydrochloric acid and allowed to stand under cooling. The precipitated crystals were collected by filtration and washed with water to give Compound (27) (174 g; yield, 97%).

Workup

  1. additionwas added
  2. temperatureunder cooling
  3. temperatureunder cooling
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-d6a5bb4bc51449a7b7edaa75906ed3c1
Source dataset
uspto-grants-1991_12
Patent number
US05071636

Reaction notes

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