Diisopropylamine → HCID 67006543, compound

HRID 564334Notes

Reaction equation

HRID 564334 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(NC(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([S:51]([C:54]23[C:67]4[C:62](=[C:63]([F:69])[CH:64]=[CH:65][C:66]=4[F:68])[O:61][CH2:60][CH:59]2[NH:58][CH2:57][CH2:56][CH2:55]3)(=[O:53])=[O:52])=[CH:47][CH:46]=1>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][C:10]([N:58]1[CH:59]2[C:54]([S:51]([C:48]3[CH:49]=[CH:50][C:45]([Cl:44])=[CH:46][CH:47]=3)(=[O:53])=[O:52])([C:67]3[C:62]([O:61][CH2:60]2)=[C:63]([F:69])[CH:64]=[CH:65][C:66]=3[F:68])[CH2:55][CH2:56][CH2:57]1)=[O:12])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670064054a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene

Product 1

HCID 67006543HCID 67006543, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

BOC-Glycine was dissolved in 150 ml of DMF. 0.5 ml of diisopropylamine was added followed by HATU (2.54 g, 6.68 mmol). The solution was stirred at room temperature for 25 minutes then 4a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene (541 mg, 1.35 mmol) was added and the reaction was stirred overnight. The reaction was quenched with water and washed with 1:1 mixture of ethyl acetate and hexanes solution. The organic layer was dried over sodium sulfate and concentrated. The product was purified by column using EtOAc/Hex. as the eluent (0/100 to 25/75 in 35 minutes). Yield: 594.6 mg, 79%. 1H NMR (CDCl3 400 MHz) δ 7.57 (d, J=8.8 Hz, 2H), 7.41 (d, J=8.8 Hz, 2H), 7.03 (td, J=8.8, 4.4 Hz, 1H), 6.57-6.49 (m, 1H), 5.60-5.55 (m, 1H), 5.35 (bs, 1H), 4.49 (dd, J=11.7, 3.7 Hz, 1H), 4.18 (dd, J=11.7, 5.9 Hz, 1H), 4.00 (s, 1H), 3.90 (d, J=5.1 Hz, 1H), 3.54 (bs, 1H), 2.95-2.80 (m, 1H), 2.65-2.56 (m, 1H), 2.52-2.41 (m, 1H), 2.13-1.98 (m, 1H), 1.51-1.40 (m, 1H), 1.40 (s, 9H).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched with water
  3. washwashed with 1:1 mixture of ethyl acetate and hexanes solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified by column
  7. customas the eluent (0/100 to 25/75 in 35 minutes)

Sources & evidence

ORD record
ord-dd22f0e4458245a9a7adf3b1743755cd
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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