Hydrochloric Acid → HCID 71515494, compound

HRID 1615419Notes

Reaction equation

HRID 1615419 reaction equation
Cl.CO.C(OC([N:11](C(OC(C)(C)C)=O)[C:12]1[C:13]([C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([C@@H:41]4[CH2:46][O:45][CH2:44][CH2:43][N:42]4C(OC(C)(C)C)=O)=[CH:37][CH:36]=3)[CH:31]=2)=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C>ClCCl>[CH:27]([S:24]([C:21]1[CH:22]=[CH:23][C:18]([C:15]2[N:14]=[C:13]([C:30]3[O:34][N:33]=[C:32]([C:35]4[CH:40]=[CH:39][C:38]([C@@H:41]5[CH2:46][O:45][CH2:44][CH2:43][NH:42]5)=[CH:37][CH:36]=4)[CH:31]=3)[C:12]([NH2:11])=[N:17][CH:16]=2)=[CH:19][CH:20]=1)(=[O:26])=[O:25])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86680659HCID 86680659, compound

Product 1

HCID 71515494HCID 71515494, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

HCl in methanol (595.7 μL of 3 M, 1.787 mmol) was added to a solution of tert-butyl (3R)-3-[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]isoxazol-3-yl]phenyl]morpholine-4-carboxylate 14 (144 mg, 0.178 mmol) in dichloromethane (5.538 mL) and the resulting solution stirred at 50° C. overnight (a yellow precipitate formed). The reaction mixture was cooled to rt and the solid was collected by filtration, washed with CH2Cl2 and dried by suction leaving product as a yellow solid. Material was recrystallised from dichloromethane and methanol (approx 3:1 ratio DCM:MeOH) to leave the product as a yellow solid (28 mg, 28% yield); 1H NMR (DMSO) d 1.18 (6H, d), 3.47 (1H, m), 3.79-3.87 (2H, m), 4.03-4.09 (2H, m), 4.57 (1H, m), 7.23 (2H, br s), 7.75 (2H, d), 7.85 (1H, s), 7.93 (2H, m), 8.12 (2H, d), 8.37 (2H, d), 8.96 (1H, s) and 9.53 (2H, br s) ppm; MS (ES+) 506.5.

Workup

  1. customformed)
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationthe solid was collected by filtration
  4. washwashed with CH2Cl2
  5. customdried by suction
  6. customleaving product as a yellow solid
  7. customMaterial was recrystallised from dichloromethane and methanol (approx 3:1 ratio DCM:MeOH)

Sources & evidence

ORD record
ord-5e2ddb21009c40309f2875e27cc0f35a
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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