Hydrochloric Acid → HCID 69019704, compound

HRID 857915Notes

Reaction equation

HRID 857915 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7](Cl)=[O:8])[CH2:3][CH2:2]1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH:19]([C:23]([OH:25])=[O:24])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.Cl>ClCCl.O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[O:8])[CH:19]([C:23]([OH:25])=[O:24])[CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2795505Oxane-4-carbonyl chlorideHCID 51758554-[(Tert-butoxy)carbonyl]piperazine-2-carboxylic acid

Product 1

HCID 69019704HCID 69019704, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Tetrahydropyran-4-carbonyl chloride was added drop wise to a mixture of piperazine-1,3-dicarboxylicacid 1-tert-butyl ester (123 g, Reference Example 63) and triethylamine (150 g) in dichloromethane (2000 ml) over a period of 0.45 hours. After stirring at room temperature for 3 days the reaction mixture was treated with water (1500 ml) and then acidified to pH 2 by addition of hydrochloric acid (37%). The organic phase was separated, then washed with aqueous sodium chloride solution (1%) and then evaporated under reduced pressure to give a yellow foam (157 g) which was recrystallised from diethyl ether and then from ethyl acetate to give the title compound (67.9 g) as white solid.

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium chloride solution (1%)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-81ceb8ba4b1f43de970c88823affb58d
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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