Hydrochloric Acid → HCID 66761059, compound

HRID 532972Notes

Reaction equation

HRID 532972 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[S:4][N:3]=1.[ClH:20]>ClCCl.CCO>[ClH:20].[CH3:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[S:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66762121HCID 66762121, compound

Product 1

HCID 66761059HCID 66761059, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

The Boc-protected intermediate 11a (0.87 g, 3.07 mmol) was stirred in dichloromethane (10 mL) and treated with 10 mL of a 2.53 M solution of HCl in EtOH. After warming to 35° C. for 2 hours, the mixture was concentrated under vacuum. The product was precipitated from IPA:MTBE (1:10). The product was recrystallized from IPA:MTBE three times to afford a high purity sample (42 mg) of white solid. MS (ESI) m/z 184 [M+1]+. NMR (CDCl3) δ 1.68-1.91 (m, 3H), 2.13-2.20 (d, 1H), 2.58 (s, 3H), 2.87-2.95 (dt, 1H), 3.14 (t, 1H), 3.25-3.28 (d, 1H), 3.54-3.59 (d, 1H), 3.65-3.73 (m, 1H), 9.10 (s, 2H).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe product was precipitated from IPA:MTBE (1:10)
  3. customThe product was recrystallized from IPA

Sources & evidence

ORD record
ord-59460864f8c3476087d91b5c317368d6
Source dataset
uspto-grants-2014_10
Patent number
US08853219B2

Reaction notes

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