1-Hydroxybenzotriazole → HCID 19610530, compound

HRID 977023Notes

Reaction equation

HRID 977023 reaction equation
[CH3:1][N:2]([NH:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:17][CH:16]=1)[C:3]([O:5]CC1C=CC=CC=1)=O.C(OC(N1CCC(C(NNC([C:50]2[CH:64]=[CH:63][C:53]([O:54][CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])=[C:52]([O:65][CH2:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH:51]=2)=O)=O)CC1)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>[Pd].CN(C=O)C.CO>[CH3:1][N:2]([NH:13][C:14](=[O:30])[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[CH:19][CH:20]=1)[C:3]([C:64]1[CH:50]=[CH:51][C:52]([O:65][CH2:66][C:67]([O:69][C:70]([CH3:71])([CH3:72])[CH3:73])=[O:68])=[C:53]([O:54][CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH:63]=1)=[O:5]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19610507HCID 19610507, compoundHCID 19610547HCID 19610547, compound

Product 1

HCID 19610530HCID 19610530, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 9, starting material step (b), the product of step (a) (440 mg), 10% Pd on C (100 mg) and methanol (40 ml) were hydrogenolysed. A mixture of the oily residue so obtained, the product of Example 2, starting material step (c) (470 mg), HBTU (460 mg), HOBT (190 mg), diisopropylethylamine (0.63 ml) and DMF (3 ml) was reacted to give a residue which was purified by column chromatography on silica, eluting with ethyl acetate/hexane, 3:2, to give t-butyl 4-[2-methyl-3-(4-t-butoxycarbonylaminomethylbenzoyl)carbazoyl]-2-(t-butoxycarbonylmethoxy)phenoxyacetate (380 mg) as a glass; NMR (DMSO-d6) 1.33 (9H, s), 1.38 (9H, s), 1.43 (9H, s), 3.20 (3H, s), 4.13 (2H, d), 4.59 (2H, s), 4.67 (2H, s), 6.83 (1H, d), 7.13 (2H, m), 7.28 (2H, d), 7.62 (2H, d), 7.40 (1H, t), 10.98 (1H, s); Mass Spectrum m/Z 666 (M+Na)+.

Workup

  1. additionA mixture of the oily residue
  2. customso obtained
  3. customwas reacted
  4. customto give a residue which
  5. customwas purified by column chromatography on silica
  6. washeluting with ethyl acetate/hexane, 3:2

Sources & evidence

ORD record
ord-a6c2357de3c7426a8d1694d2732c4692
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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