Benzyl Bromide → HCID 178511530, compound

HRID 1486200Notes

Reaction equation

HRID 1486200 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.CCOCC>[NH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][C:16]([O:18][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:17])[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 112538972-((1s,4s)-4-(((Tert-butoxy)carbonyl)amino)cyclohexyl)acetic acid

Product 1

HCID 178511530HCID 178511530, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(tert-butoxycarbonylamino)cyclohexyl]acetic acid (1.0 g, 4 mmol) in DMF (10 mL) was added K2CO3 (600 mg, 4 mmol) followed by benzyl bromide (0.5 mL, 4.2 mmol). The resulting mixture was stirred for 16.75 hours, diluted with ether, washed with water (2×) followed by brine, dried over magnesium sulfate and concentrated. The residue was taken up in dichloromethane (12 mL). To this solution was added TFA (3 mL). The resulting solution was stirred for 2.5 hours then concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed with saturated sodium bicarbonate solution followed by brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound as a white solid.

Workup

  1. washwashed with water (2×)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. additionTo this solution was added TFA (3 mL)
  5. stirringThe resulting solution was stirred for 2.5 hours
  6. concentrationthen concentrated under reduced pressure
  7. washwashed with saturated sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6e7e67318684a20839547b4980b7ba7
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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