Sulfuric Acid → HCID 178454420, compound

HRID 538047Notes

Reaction equation

HRID 538047 reaction equation
C(OC(=O)[NH:7][CH:8]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:9][C:10](=[O:32])[NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:23][CH2:22]2)=[O:20])[CH2:15][CH2:14]1)(C)(C)C.OS(O)(=O)=O>C(Cl)Cl.[OH-].[Na+]>[NH2:7][CH:8]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:9][C:10]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:23][CH2:22]2)=[O:20])[CH2:15][CH2:14]1)=[O:32]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 178454421HCID 178454421, compound

Product 1

HCID 178454420HCID 178454420, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (2-{[trans-4-(4-Isobutyryl-piperazine-1-carbonyl)-cyclohexylmethyl]-carbamoyl}-1-phenyl-ethyl)-carbamic acid tert-butyl ester (0.65 g, 1.21 mmol) in DCM (20 mL), H2SO4 (0.16 mL, 3.02 mmol) was added and the reaction was left stirring at room temperature for 18 hours. The mixture was diluted with 20 mL of NaOH 2N solution and the aqueous phase was concentrated under reduced pressure to give a white solid. The titled compound was extracted with EtOH. The solvent was removed under reduced pressure affording 0.13 g of the titled compound (24% yield).

Workup

  1. waitthe reaction was left
  2. concentrationthe aqueous phase was concentrated under reduced pressure
  3. customto give a white solid
  4. extractionThe titled compound was extracted with EtOH
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f68395ffa1bd4e2e9464f8b45e02fe1d
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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