Ethyl Acetate → HCID 70045463, compound

HRID 1602719Notes

Reaction equation

HRID 1602719 reaction equation
C(OC(N1CCC(C(N[NH:17][C:18]([C:20]2[CH:34]=[CH:33][C:23]([O:24][CH2:25][C:26](OC(C)(C)C)=[O:27])=[C:22]([O:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:21]=2)=[O:19])=O)CC1)=O)(C)(C)C.CN(C(ON1N=N[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N([OH:77])N=NC=2C=1.C([N:81]([CH:84](C)C)CC)(C)C.CN(N)C(O[CH2:92][C:93]1[CH:98]=CC=C[CH:94]=1)=O.[C:100]([O:103][CH2:104]C)(=[O:102])C>CN(C=O)C>[CH3:84][N:81]([NH:17][C:18](=[O:19])[C:20]1[CH:34]=[CH:33][C:23]([O:24][CH2:25][C:26]([O:77][C:93]([CH3:92])([CH3:94])[CH3:98])=[O:27])=[C:22]([O:35][CH2:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH:21]=1)[C:100]([O:103][CH2:104][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:102]

Participants

8

Reactant 6

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11217590Benzyl 1-methylhydrazinecarboxylateHCID 19610507HCID 19610507, compound

Product 1

HCID 70045463HCID 70045463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 2, starting material step (c) (470 mg), HBTU (460 mg) and HOBT (190 mg) in DMF (3 ml) under argon was added diisopropylethylamine (0.63 ml). After 2-3 minutes the resultant pale yellow reaction mixture was added to benzyl 2-methylcarbazate (Dutta, A. S. et al (1975), J. Chem. Soc. Perkin Trans. I, 1712-20) (200 mg). The reaction mixture was stirred at ambient temperature under argon for 3.5 hours then diluted with ethyl acetate (50 ml) and washed with water, dilute KHSO4 (aq.) and dilute NaOH (aq.) and water, dried (MgSO4) and evaporated to give benzyl 2-methyl-3-(3,4-di-t-butoxycarbonylmethoxybenzoyl)carbazate (0.61 g) as a glass; NMR Spectrum (DMSO-d6) 1.43 (18H, s), 3.13 (3H, br s), 4.70 (2H, s), 4.75 (2H, s), 5.02-5.20 (2H, br), 6.99 (1H, m), 7.20-7.50 (7H, m), 10.68 (1H, br); Mass Spectrum m/Z 544 (M+). In the ambient temperature NMR spectrum, ancillary signals attributable to rotamers were observed.

Workup

  1. washwashed with water, dilute KHSO4 (aq.) and dilute NaOH (aq.) and water
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-cac07175f5a045dfa2d10a58152b1406
Source dataset
uspto-grants-1999_11
Patent number
US05981531

Reaction notes

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