Diisopropylethylamine → {(S)-1-[(S)-1-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 1481900Notes

Reaction equation

HRID 1481900 reaction equation
[N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:7])[C@H:2]([C:4]([OH:6])=O)[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[NH2:55][C@@H:56]1[C:62](=[O:63])[N:61]([CH2:64][C:65]2[C:74]3[C:69](=[CH:70][C:71]([Br:75])=[CH:72][CH:73]=3)[CH:68]=[CH:67][C:66]=2[O:76][CH3:77])[C:60]2[CH:78]=[CH:79][CH:80]=[CH:81][C:59]=2[NH:58][CH2:57]1>CN(C=O)C>[C:11]([O:10][C:8](=[O:9])[N:1]([C@H:2]([C:4](=[O:6])[NH:55][C@@H:56]1[C:62](=[O:63])[N:61]([CH2:64][C:65]2[C:74]3[C:69](=[CH:70][C:71]([Br:75])=[CH:72][CH:73]=3)[CH:68]=[CH:67][C:66]=2[O:76][CH3:77])[C:60]2[CH:78]=[CH:79][CH:80]=[CH:81][C:59]=2[NH:58][CH2:57]1)[CH3:3])[CH3:7])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90221253(S)-3-amino-1-(6-bromo-2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate

Product 1

HCID 72713837{(S)-1-[(S)-1-(6-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl esterYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-N-Me-Ala-OH (650 mg, 3.19 mmol), HATU (1.32 g, 3.48 mmol) and DIPEA (1.52 mL, 8.72 mmol) were added to a solution of (S)-3-amino-1-(6-bromo-2-methoxy-naphthalen-1-ylmethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one trifluoroacetate (1.6 g, 2.90 mmol) in DMF (10 mL). After 18 the mixture was evaporated and the mixture diluted with ethyl acetate. The mixture was washed with water, brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography to afford the title compound (1.6 g, 88%) as a yellow solid. LC-MS: 611 (M+H).

Workup

  1. customAfter 18 the mixture was evaporated
  2. additionthe mixture diluted with ethyl acetate
  3. washThe mixture was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-35c0433771ca418986ebe4ad94b4f8c0
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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