Sodium Hydroxide → HCID 86726700, compound

HRID 1499455Notes

Reaction equation

HRID 1499455 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([NH:30][C:31]1[S:35][C:34]([C:36]2[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=2[F:43])=[N:33][C:32]=1[C:44]([NH:46][C:47]1[C:48]([N:57]2[CH2:62][CH2:61][CH2:60][C@H:59]([NH:63][C:64](=[O:70])[O:65][C:66]([CH3:69])([CH3:68])[CH3:67])[CH2:58]2)=[C:49]2[CH2:55][CH2:54][CH:53]([OH:56])[C:50]2=[N:51][CH:52]=1)=[O:45])=[O:29])([CH3:26])([CH3:25])[CH3:24].[OH-].[Na+]>C(Cl)Cl.CO>[C:23]([O:27][C:28]([NH:30][C:31]1[S:35][C:34]([C:36]2[C:37]([F:43])=[CH:38][CH:39]=[CH:40][C:41]=2[F:42])=[N:33][C:32]=1[C:44]([NH:46][C:47]1[C:48]([N:57]2[CH2:62][CH2:61][CH2:60][C@H:59]([NH:63][C:64](=[O:70])[O:65][C:66]([CH3:69])([CH3:68])[CH3:67])[CH2:58]2)=[C:49]2[CH2:55][CH2:54][C:53](=[O:56])[C:50]2=[N:51][CH:52]=1)=[O:45])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 86726701HCID 86726701, compound

Product 1

HCID 86726700HCID 86726700, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (12 mg, 0.028 mmol) was added to a solution of tert-butyl {(3S)-1-[3-({[5-[(tert-butoxycarbonyl)amino]-2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]piperidin-3-yl}carbamate (15 mg, 0.022 mmol) in DCM (0.098 mL). The reaction mixture was stirred at room temperature for 1 h. The solution was neutralized with 1 M NaOH, diluted with MeOH and filtered. The mixture was then concentrated under reduced pressure and the crude product was purified by preparative LC-MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min., eluting with a gradient of MeCN and water with 0.15% NH4OH) to give sub-title compound as off-white powder (7.5 mg, 50%). LCMS calc. for C33H39F2N6O6S (M+H)+: m/z=685.3. Found: 685.1.

Workup

  1. filtrationfiltered
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customthe crude product was purified by preparative LC-MS (XBridge™ preparative C18 5 μm 30×10 mm OBD™ column, flow rate 60 mL/min.
  4. washeluting with a gradient of MeCN and water with 0.15% NH4OH)

Sources & evidence

ORD record
ord-945b51f9347d4bf089e632a2c735a3d0
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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