Diisopropylethylamine → HCID 59444213, compound

HRID 1888116Notes

Reaction equation

HRID 1888116 reaction equation
C(O[C:6]([NH:8][C:9]1([CH2:15][C:16]([OH:18])=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])(C)(C)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@@:26]2([OH:34])[CH2:31][CH2:30][NH:29][CH2:28][C:27]2([CH3:33])[CH3:32])=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=2N=N1>CN(C=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C@@:26]2([OH:34])[CH2:31][CH2:30][N:29]([C:16](=[O:18])[CH2:15][C:9]3([NH:8][C:6](=[O:7])[C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[CH2:28][C:27]2([CH3:32])[CH3:33])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 170401964-[(tert-Butoxycarbonyl)amino]-4-(carboxymethyl)tetrahydro-2H-pyran, 4-Amino-4-(carboxymethyl)tetrahydro-2H-pyran, N-BOC protectedHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

Product 1

HCID 59444213HCID 59444213, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-yl)acetic acid (step 2, 0.125 g, 0.48 mmol) in anhydrous DMF (1 mL) was sequentially added (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (0.182 g, 0.48 mmol), diisopropylethylamine (0.17 mL, 0.96 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (0.225 g, 0.50 mmol) at room temperature. Upon completion of addition, the reaction mixture was stirred at room temperature for 20 h and then partitioned between ethyl acetate (20 mL) and 1N HCl (10 mL). The ethyl acetate layer was separated, washed sequentially with 1N NaOH (10 mL), brine (10 mL), dried over sodium sulfate and concentrated to yield a residue. The residue was purified using a pre-packed silica gel column (40 g) employing hexane and ethyl acetate. The desired fractions were collected and concentrated under reduced pressure to yield the title compound (0.175 g) as a foamy solid. MS (ESI+)=481.1 (M+H)+.

Workup

  1. customat room temperature
  2. additionUpon completion of addition
  3. custompartitioned between ethyl acetate (20 mL) and 1N HCl (10 mL)
  4. customThe ethyl acetate layer was separated
  5. washwashed sequentially with 1N NaOH (10 mL), brine (10 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto yield a residue
  9. customThe residue was purified
  10. customThe desired fractions were collected
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a33bc379b32b413db928d85b83e6d59a
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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