Di-tert-butyl dicarbonate → HCID 58789062, compound

HRID 708801Notes

Reaction equation

HRID 708801 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15]([NH2:20])=[N:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:28](C(OC(C)(C)C)=O)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=O>C(#N)C.CN(C1C=CN=CC=1)C>[C:32]([O:31][C:29]([N:20]([C:15]1[C:16]2[C:11](=[CH:10][C:9]([N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:18]([F:19])[CH:17]=2)[CH:12]=[CH:13][N:14]=1)[C:29](=[O:28])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 58789219HCID 58789219, compound

Product 1

HCID 58789062HCID 58789062, compoundYield 148.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of Intermediate 4A (1.73 g, 3.78 mmol) in acetonitrile (20 mL) was added BOC2O (1.229 mL, 5.29 mmol) followed by TEA (0.527 mL, 3.78 mmol) and DMAP (0.092 g, 0.756 mmol), then the suspension was stirred at rt for 1 h. Solvent was removed under vacuum and the residue purified on Isco (120 g) eluting with 0 to 75% EtOAc/hexanes to give Intermediate 4B (2.185 g, 3.92 mmol, 104% yield) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 1.38 (s, 18H) 4.54 (s, 4H) 7.04 (d, J=8.53 Hz, 1H) 7.28-7.40 (m, 11H) 7.53 (d, J=14.05 Hz, 1H) 8.25 (d, J=5.77 Hz, 1H); MS (ESI) m/z: 558.2 [M+1]+.

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue purified on Isco (120 g)
  3. washeluting with 0 to 75% EtOAc/hexanes

Sources & evidence

ORD record
ord-254b120b0e0b4840922343d7d1c3adfe
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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