Dimethylformamide → HCID 131721364, compound

HRID 618155Notes

Reaction equation

HRID 618155 reaction equation
[C:1]([C:8]1[C:13]([NH2:14])=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH:25]2[CH2:27][CH2:26]2)[CH2:21][C:22](O)=[O:23])=[O:19])[CH:11]=[CH:10][N:9]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.F[P-](F)(F)(F)(F)F.[N:42]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:46]2C=CC=C[C:45]=2N=N1.CN(C=[O:66])C>>[CH2:33]([O:32][C:31](=[O:66])[CH2:30][C@@H:46]([CH3:45])[NH:42][C:22](=[O:23])[CH2:21][N:20]([C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C:13]=1[NH2:14])[CH:25]1[CH2:27][CH2:26]1)[CH3:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86754478HCID 86754478, compound

Product 1

HCID 131721364HCID 131721364, compound

Procedure

Acid 7-4 (100 mg, 0.26 mmol), amine hydrochloride 9-1 (see U.S. Pat. No. 5,281,585) (49 mg, 0.29 mmol), NMM (117 μL, 1.1 mmol) and BOP (176 mg, 0.40 mmol) were combined in 1.3 mL DMF. After 3 d the mixture was concentrated, redissolved in EtOAc, washed with water (2×), 5% KHSO4, sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, EtOAc) provided 9-2 as a colorless oil.

Workup

  1. concentrationAfter 3 d the mixture was concentrated
  2. dissolutionredissolved in EtOAc
  3. washwashed with water (2×), 5% KHSO4, sat. NaHCO3, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7875abe7c5bb444f8ff65ecccea90421
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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