Diisopropylethylamine → HCID 86708066, compound

HRID 1524363Notes

Reaction equation

HRID 1524363 reaction equation
[NH2:1][CH2:2][C:3]([F:41])([F:40])[CH2:4][CH2:5][C@H:6]([N:16]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:42][O:43][C:44]([NH:46][C@H:47]([C:61](O)=[O:62])[CH:48]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:45].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:9]([O:8][CH2:7][C@@H:6]([N:16]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([CH2:26][O:27][Si:28]([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:29])[CH3:30])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:5][CH2:4][C:3]([F:41])([F:40])[CH2:2][NH:1][C:61](=[O:62])[C@H:47]([CH:48]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[NH:46][C:44]([O:43][CH3:42])=[O:45])([C:12]([CH3:13])([CH3:15])[CH3:14])([CH3:10])[CH3:11]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 86708065HCID 86708065, compound

Product 1

HCID 86708066HCID 86708066, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the material from Step 10 (42 mg, 0.066 mmol), N-(methoxycarbonyl)-β-phenyl-L-phenylalanine (39 mg, 0.132 mmol), and N,N-diisopropylethylamine (46 μL, 0.264 mmol) in 1 mL of DMF was added BOP (58 mg, 0.132 mmol). The reaction mixture was stirred at room temperature overnight, poured into saturated aqueous NaHCO3, and extracted with EtOAc (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes (0 to 100%) to afford the title compound.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2b66940b058c4a8ab713ebc5c84e20db
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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