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Diisopropylethylamine → 4-[1-(3-Chloro-phenyl)-2-hydroxy-ethylcarbamoyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1295674
Notes
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Reaction equation

HRID 1295674 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.[CH:35]1[CH:40]=[C:39]([Cl:41])[CH:38]=[C:37]([C@H:42]([NH2:45])[CH2:43][OH:44])[CH:36]=1>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:2](=[O:4])[NH:45][CH:42]([C:37]2[CH:36]=[CH:35][CH:40]=[C:39]([Cl:41])[CH:38]=2)[CH2:43][OH:44])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 59694427(S)-2-amino-2-(3-chlorophenyl)ethanol

Product 1

HCID 694145564-[1-(3-Chloro-phenyl)-2-hydroxy-ethylcarbamoyl]-piperazine-1-carboxylic acid tert-butyl esterYield 39.2%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Triphosgene (264 mg, 0.89 mmol) was dissolved in methylene chloride (20 mL) and the mixture cooled to −78° C. under nitrogen atmosphere. A mixture of t-butoxycarbonyl-piperazine (500 mg, 2.4 mmol) and diisopropylethylamine (2 mL) in CH2Cl2 was added dropwise to the cold stirring solution over 30 minutes. When the addition was complete, a mixture of (S)-(+)-3-chlorophenylglycinol (500 mg, 2.4 mmol) and DIEA (2 mL) in CH2CL2 (5 mL) was added. The reaction warmed to ambient temperature and concentrated in vacuo. The resulting residue was purified by preparative HPLC (Gilson: Column=CombiHT SB-C189 5 μM 21.2 mm×100 mm, eluent=0.1% TFA MeCN/H2O gradient) to afford the desired compound as a yellow oil (134 mg) Rt=6.72 minutes.

Workup

  1. additionwas added dropwise to the cold stirring solution over 30 minutes
  2. additionWhen the addition
  3. additionwas added
  4. temperatureThe reaction warmed to ambient temperature
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by preparative HPLC (Gilson: Column=CombiHT SB-C189 5 μM 21.2 mm×100 mm, eluent=0.1% TFA MeCN/H2O gradient)

Sources & evidence

ORD record
ord-6463d26336224aa188167b31626e03be
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07244735B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes