2-(2-(Benzylcarbamoyl)-1-methylhydrazinyl)acetic acid → N-benzyl-2-(2-((S)-3-(4-tert-butoxyphenyl)-1-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-2-methylhydrazinecarboxamide

HRID 718933Notes

Reaction equation

HRID 718933 reaction equation
[CH2:1]([NH:8][C:9]([NH:11][N:12]([CH2:14][C:15]([OH:17])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=NNC=2C=CC=1.[NH2:28][C@@H:29]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[CH:56][CH:55]=1)[C:30]([N:32]([C@@H:44]([CH3:52])[CH:45]([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48])[CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)=[O:31]>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([NH:11][N:12]([CH2:14][C:15]([NH:28][C@@H:29]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[CH:56][CH:55]=1)[C:30]([N:32]([C@@H:44]([CH3:52])[CH:45]([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48])[CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)=[O:31])=[O:17])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 533974892-(2-(Benzylcarbamoyl)-1-methylhydrazinyl)acetic acidHCID 67075242HCID 67075242, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67075567N-benzyl-2-(2-((S)-3-(4-tert-butoxyphenyl)-1-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-2-methylhydrazinecarboxamideYield 90%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2-(2-(benzylcarbamoyl)-1-methylhydrazinyl)acetic acid (Compound VI-3) 182 mg (0.77 mmol), hydroxybenzotriazole 104 mg (0.77 mmol) and 1-ethyl-3-(3-s dimethylaminopropyl)carbodiimide 148 mg (0.77 mmol) in dichloromethane 3 ml, a solution of (S)-2-amino-3-(4-tert-butoxyphenyl)-N—((S)-1,1-diethoxypropan-2-yl)-N-(naphthalen-1-ylmethyl)propanamide (Compound IV-2) 260 mg (0.51 mmol) and 4-dimethylaminopyridine 31 mg (0.26 mmol) in dichloromethane 3 ml was added and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate 50 ml and washed with saturated sodium bicarbonate 50 ml, water 50 ml and brine 50 ml. The organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on Buch silica gel column chromatography (chloroform:methanol=95:5) to obtain the title compound 333 mg (90%).

Workup

  1. washwashed with saturated sodium bicarbonate 50 ml, water 50 ml and brine 50 ml
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified on Buch silica gel column chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-b246d68d0481497e870c8964c3124828
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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