Water → HCID 86666946, compound

HRID 511027Notes

Reaction equation

HRID 511027 reaction equation
C(OC([NH:11][CH:12]([C:14]1[C:15]([O:33][CH3:34])=[C:16]([CH:22]2[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]2)[C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=1)[CH3:13])=O)C1C=CC=CC=1.O.[H][H]>CO.Cl.[Pt]>[NH2:11][CH:12]([C:14]1[C:15]([O:33][CH3:34])=[C:16]([CH:22]2[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:23]2)[C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=1)[CH3:13]

Participants

7

Reactant 3

HCID 962WaterHCID 86666947HCID 86666947, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86666946HCID 86666946, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalyst2×HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 3-[3-(1-{[(benzyloxy)carbonyl]amino}ethyl)-5,6-dichloro-2-methoxyphenyl]azetidine-1-carboxylate [peak 2 isomer from step 6] (0.29 g, 0.57 mmol) in methanol (17 mL) and 0.25 M HCl in water (5.7 mL, 1.4 mmol) was degassed with nitrogen, treated with 5% Pt/C (Degussa type) (73 mg, 25 wt %), and stirred under a balloon of hydrogen for 1 hour. The reaction mixture was treated with additional 5% Pt/C (Degussa type) (100 mg) and stirred under a balloon of hydrogen for an additional 1 hour. The reaction mixture was filtered over Celite and neutralized with saturated sodium bicarbonate solution. The reaction mixture was concentrated to remove the methanol, extracted with dichloromethane, and concentrated to give the desired product (0.21 g, 99%) as a colorless foam that was used without further purification. LCMS for C13H14C12NO3 (M−[NH2]−[t-Bu]+H)+: m/z=302.0, 304.0. Found: 301.9, 304.0.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. concentrationThe reaction mixture was concentrated
  3. customto remove the methanol
  4. extractionextracted with dichloromethane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f413868ba604329a12738ed9d7953b0
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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