Hydrogen Bromide → HCID 86738927, compound

HRID 2166799Notes

Reaction equation

HRID 2166799 reaction equation
C([NH:8][C@H:9]([C:14]([NH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23](=[O:27])[O:24]2)=[CH:19][CH:18]=1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])(OC(C)(C)C)=O.[BrH:34]>C(O)(=O)C.C(O)C>[NH2:8][C@H:9]([C:14]([NH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23](=[O:27])[O:24]2)=[CH:19][CH:18]=1)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13].[BrH:34]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 22823403HCID 22823403, compound

Product 1

HCID 86738927HCID 86738927, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The product of Example I, above, (175.1 mg, 0.39 mmol) was dissolved at room temperature in 2 mL of 32% hydrobromic acid in acetic acid. After 10 min., 40 mL of 2/1 ether/petroleum ether was added. The precipitated solid was separated and dried overnight at room temperature and 5 Pa to yield a glassy, orange foam which was twice dissolved in 1 mL of absolute ethanol and reprecipitated by addition of 30 mL of ether. After drying overnight at room temperature and 5 Pa, there remained 73 mg (44.5%) of white solid; TLC (SiO2 : 10% methanol in methylene chloride) Rf =0.63; mp=190.1°; NMR (CD3OD) δ(LeuCH3)=1.08 D (6), J=5 Hz, δ(LeuCH2) 1.86 D (2), δ(LeuCH)=4.0 M (1), δ(ArH)=7.7 M (9); IR (KBr) C=O=1700 cm-1.

Workup

  1. customThe precipitated solid was separated
  2. customdried overnight at room temperature
  3. custom5 Pa to yield a glassy, orange foam which
  4. customreprecipitated by addition of 30 mL of ether
  5. customAfter drying overnight at room temperature

Sources & evidence

ORD record
ord-cf60f153cd2d4d70bc6c2f10048a99cb
Source dataset
uspto-grants-1983_06
Patent number
US04388233

Reaction notes

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