Hydrochloric Acid → HCID 42600053, compound

HRID 875268Notes

Reaction equation

HRID 875268 reaction equation
[OH:1][C:2]12[CH2:35][CH2:34][C@:33]3([CH3:36])[C:28](=[C:29]([CH3:37])[CH2:30][CH2:31][CH2:32]3)[C@@H:3]1[O:4][C:5](=[O:27])[CH:6]2[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[C:16]=2[CH2:25][OH:26])[CH2:10][CH2:9]1.[K+].[Br-].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+].Cl.[O-:55]Cl=O.[Na+]>O.C(OCC)(=O)C>[OH:1][C:2]12[CH2:35][CH2:34][C@:33]3([CH3:36])[C:28](=[C:29]([CH3:37])[CH2:30][CH2:31][CH2:32]3)[C@@H:3]1[O:4][C:5](=[O:27])[CH:6]2[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[C:16]=2[C:25]([OH:55])=[O:26])[CH2:10][CH2:9]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 253877Potassium BromideHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 23668197Sodium ChloriteHCID 42599806HCID 42599806, compound

Product 1

HCID 42600053HCID 42600053, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

Ethyl acetate (10 mL) was added to a mixture of compound of example 38 (150 mg, 0.29 mol) and KBr in water (0.5 M, 0.24 mL), followed by addition of TEMPO (3.12 mg, 0.02 mmol). A solution of 12% NaClO in water (27 mg, 0.36 mmol) was added dropwise to the mixture over 30 minutes at 5° C. at pH of 8.0-10.0. Stirring was continued for 30 minutes at room temperature (25° C.). Then, the pH was adjusted to 5.0 by addition of 35% hydrochloric acid, followed by addition of 25% NaClO2 in water (32.8 mg, 0.36 mmol) over 30 minutes maintaining the temperature of 27-33° C. Stirring was continued for 3 hours at room temperature (25° C.). The product was extracted with ethyl acetate (3×50 mL), washed with brine, followed by concentration to obtain the title compound.

Workup

  1. custom(25° C.)
  2. stirringStirring
  3. waitwas continued for 3 hours at room temperature
  4. custom(25° C.)
  5. extractionThe product was extracted with ethyl acetate (3×50 mL)
  6. washwashed with brine
  7. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-35c0add49f54443ba8cf85f797d1b3a6
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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