Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 123430768, compound

HRID 1096675Notes

Reaction equation

HRID 1096675 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C@@H:15]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C1C2C(COC(N[C@H:45]([CH2:50][NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:46][C:47](O)=[O:48])=O)C3C(=CC=CC=3)C=2C=CC=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][C:69]=2N=N1.CN(C(ON1N=N[C:96]2C=CC=N[C:95]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1CCOCC1>[CH:24]1[C:25]2[CH:26]([NH:21][C@@H:45]([CH2:46][C:47]([N:17]3[CH2:18][CH2:19][CH2:20][C@@H:15]([C:7]4[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[N:8]=4)[CH2:16]3)=[O:48])[CH2:50][NH:51][C:52](=[O:53])[O:54][C:55]([CH3:57])([CH3:58])[CH3:56])[C:74]3[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=3)[C:96]=2[CH:95]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17040124(3S)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acidHCID 66786519HCID 66786519, compound

Product 1

HCID 123430768HCID 123430768, compound

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

Piperidine (R)-1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole (138C) (3.19 g, 11.3 mmol) was acylated with the protected butanoic acid 138B (5 g, 11.4 mmol) in N-methylmorpholine using the standard BOP coupling reaction similar to HATU procedure of Example 7, Step E yielding tert-butyl (S)-2-(9H-fluoren-9-ylamino)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutylcarbamate (1380) (7.9 g, 11.4 mmol). ESI-MS: m/z 696.6 (MH+).

Sources & evidence

ORD record
ord-a2c4c4880f4f4dd8826062aa0599d843
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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