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Ethyl Acetate → 2-{(3S)-7-Bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetamide

HRID 1054190
Notes
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Reaction equation

HRID 1054190 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C:14]([C:16]3[CH:17]=[CH:18][C:19]4[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=4[CH:26]=3)=[O:15])[C@@H:7]([CH2:10][C:11]([OH:13])=O)[CH2:8][O:9][C:4]=2[CH:3]=1.C1C[N:32]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-].CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C:14]([C:16]3[CH:17]=[CH:18][C:19]4[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=4[CH:26]=3)=[O:15])[C@@H:7]([CH2:10][C:11]([NH2:32])=[O:13])[CH2:8][O:9][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724699PyBOPHCID 118599730{(3S)-7-Bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acid2×

Product 1

HCID 1185997662-{(3S)-7-Bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetamide
Yield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{(3S)-7-Bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acid (Intermediate 29a, 160 mg, 0.36 mmol) was dissolved in DCM (3 mL). PyBOP (223 mg, 0.43 mmol) and TEA (0.248 mL, 1.79 mmol) was added followed by NH4Cl (77 mg, 1.43 mmol). The mixture was stirred at rt over weekend. EtOAc (40 mL) was added. Washed with sat. aq. Na2CO3 (2×30 mL), HCl (0.5M, 20 mL) and brine (20 mL). Dried through a phase separator and evaporated under reduced pressure. The residue was purified using a SFC2-MS system and eluting with MeOH on a Waters Viridis 2-EP column 5μ30×250 mm. Pooling of homogenous fraction and removal of solvents in vacuo gave the title compound (46.1 mg, 28.9%).

Workup

  1. washWashed with sat. aq. Na2CO3 (2×30 mL), HCl (0.5M, 20 mL) and brine (20 mL)
  2. customDried through a phase separator
  3. customevaporated under reduced pressure
  4. customThe residue was purified
  5. washeluting with MeOH on a Waters Viridis 2-EP column 5μ30×250 mm
  6. customPooling of homogenous fraction and removal of solvents in vacuo

Sources & evidence

ORD record
ord-9a7ae3f6a0d04dc18b76bd8b061846f6
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394291B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes