Diisopropylethylamine → HCID 178446307, compound

HRID 425124Notes

Reaction equation

HRID 425124 reaction equation
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:29][C:30](=[O:60])[CH2:31][C@H:32]([NH2:59])[C:33]([N:35]([CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[C:49]2[NH:53][N:52]=[N:51][N:50]=2)=[CH:39][CH:38]=1)=[O:34].C([S:64][CH2:65][CH:66]([CH2:70][CH:71]([CH3:73])[CH3:72])[C:67](O)=[O:68])(=O)C.CCN(C(C)C)C(C)C>CN(C=O)C>[SH:64][CH2:65][CH:66]([CH2:70][CH:71]([CH3:73])[CH3:72])[C:67]([NH:59][C@H:32]([C:33]([N:35]([CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:36][C:37]1[CH:38]=[CH:39][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[C:49]2[NH:53][N:52]=[N:51][N:50]=2)=[CH:41][CH:42]=1)=[O:34])[CH2:31][C:30]([OH:29])=[O:60])=[O:68]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 130175572-[(Acetylthio)methyl]-4-methylpentanoic acidHCID 178446308HCID 178446308, compound

Product 1

HCID 178446307HCID 178446307, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

BOP (88 mg, 0.2 mmol) was added to a solution of (S)-3-amino-N-pentyl-N-[2′-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]succinamic acid methyl ester (100 mg, 0.2 mmol), 2-acetylsulfanylmethyl-4-methylpentanoic acid (41 mg, 0.2 mmol) and DIPEA (34 μL) in DMF (1.5 mL) at room temperature. After 10 minutes, DIPEA (30 μL) was added. After 4 hours, the mixture was concentrate in vacuo. A solution of the concentrate in MeOH (1.0 mL), 1M aq. NaOH (1.0 mL) and 6M aq. NaOH (0.1 mL) was stirred under a nitrogen atmosphere at room temperature. After 3 hours, the mixture was neutralized with 6M aq. HCl, and was concentrated in vacuo. Reverse phase HPLC afforded the title compound (11.9 mg). MS m/z: [M+H]+ calcd for C30H40N6O4S, 581.28. found 581.4.

Workup

  1. waitAfter 4 hours
  2. concentrationthe mixture was concentrate in vacuo
  3. concentrationA solution of the concentrate in MeOH (1.0 mL)
  4. waitAfter 3 hours
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-ecbae4fff43b4d8c9eceb6736244ebf6
Source dataset
uspto-grants-2012_01
Patent number
US08106082B2

Reaction notes

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