Dimethylformamide → Benzyl 3-(4-t-butoxycarbonylmethoxybenzoyl)carbazate

HRID 977025Notes

Reaction equation

C[O:2][C:3]([CH2:5][O:6]C1C=CC(C(O)=O)=CC=1)=[O:4].CN(C(ON1N=N[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=C[C:43]2N(O)N=N[C:44]=2[CH:45]=1.[CH:50](N(C(C)C)CC)(C)C.[C:59]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)(=[O:62])[NH:60][NH2:61].CN([CH:74]=[O:75])C>>[C:44]([O:4][C:3]([CH2:5][O:6][C:25]1[CH:26]=[CH:27][C:28]([C:74]([NH:61][NH:60][C:59]([O:63][CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:62])=[O:75])=[CH:29][CH:30]=1)=[O:2])([CH3:43])([CH3:45])[CH3:50]

Participants

Reactant 6

HCID 6228Dimethylformamide

HCID 757711-Hydroxybenzotriazole

HCID 79242Benzyl carbazate

HCID 81531Diisopropylethylamine

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 138161424-(2-methoxy-2-oxoethoxy)benzoic acid

Product 1

HCID 19610493Benzyl 3-(4-t-butoxycarbonylmethoxybenzoyl)carbazate

Procedure

In a similar manner to Example 9, starting material step (a), 4-methoxycarbonylmethoxybenzoic acid (580 mg), HBTU (1.04 g), HOBT (420 mg), diisopropylethylamine (1.41 ml), DMF (7.5 ml) and benzyl carbazate (500 mg) were reacted to give benzyl 3-(4-t-butoxycarbonylmethoxybenzoyl)carbazate (550 mg) as an off-white solid; NMR Spectrum (DMSO-d6) 3.70 (3H, s), 4.88 (2H, s), 5.11 (2H, s), 7.03 (2H, d), 7.82 (2H, d), 7.38 (5H, m), 9.28 (1H, br s), 10.20 (1H, br s); Mass Spectrum m/z 359 (M+H)+.

Workup

customwere reacted

Sources & evidence

ORD record: ord-881a74f2d45943b3b958c125e2f841e9
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612373

Reaction notes

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