Triethylamine → HCID 71158281, compound

HRID 1592352Notes

Reaction equation

HRID 1592352 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:4]([CH2:19][N:20]([CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:21][CH2:22][CH3:23])[CH2:3]1.CCN(CC)CC.[C:41](Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43]>C(Cl)Cl>[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][CH2:24][N:20]([CH2:19][C@@H:4]2[CH2:3][C@H:2]([NH:1][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:7][CH2:6][C@H:5]2[NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:21][CH2:22][CH3:23])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 71158282HCID 71158282, compound

Product 1

HCID 71158281HCID 71158281, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl(1R,2S,4R)-4-amino-2-(((3-(4-fluorophenyl)propyl)(propyl)-amino)methyl)-cyclohexylcarbamate (1.1 g, 2.4 mmol) and Et3N (0.3 g, 3 mmol) in CH2Cl2 (50 ml) was cooled in an ice bath and treated drop-wise with pivaloyl chloride (0.32 g, 2.6 mmol). The solution is stirred for 30 minutes and then washed successively with saturated sodium bicarbonate, 0.5 N NaOH, and brine. The solution was dried over sodium sulfate, filtered and the solvent removed on a rotary evaporator. This chromatographed on silica gel to (0.3:2.7:97 NH4OH/MeOH/CH2Cl2) to give 0.85 g of white solid. MS: (M+H)+=540.38.

Workup

  1. washwashed successively with saturated sodium bicarbonate, 0.5 N NaOH, and brine
  2. dry with materialThe solution was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed on a rotary evaporator
  5. customThis chromatographed on silica gel to (0.3:2.7:97 NH4OH/MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-14cf39a912b44d77a3b02b8c3af51652
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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