Hydrochloric Acid → HCID 58375237, compound

HRID 536693Notes

Reaction equation

HRID 536693 reaction equation
[BH4-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([N:14]3[CH2:21][CH2:20][C@:19]4([CH3:24])[C@@H:22]([CH3:23])[C@H:15]3[C:16](=[O:30])[C:17]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:18]=34)=[O:13])=[CH:11][C:6]=2[NH:5][CH:4]=1.Cl>C(O)C>[N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([N:14]3[CH2:21][CH2:20][C@:19]4([CH3:24])[C@@H:22]([CH3:23])[C@H:15]3[CH:16]([OH:30])[C:17]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:18]=34)=[O:13])=[CH:11][C:6]=2[NH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67346769HCID 67346769, compound

Product 1

HCID 58375237HCID 58375237, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (50 mg) is added to a solution of (2S,6R,11R)-3-(3H-benzoimidazole-5-carbonyl)-8-hydroxy-6,11-dimethyl-3,4,5,6-tetrahydro-2H-2,6-methano-benzo[d]azocin-1-one (50 g) in ethanol (3 mL). The resulting mixture is stirred at ambient temperature overnight. Then, the solution is cooled in an ice bath and 1 M hydrochloric acid (0.5 mL) is added. After stirring for 5 min, the resulting mixture is concentrated and the residue is purified by HPLC on reversed phase (MeCN/H2O/NH3).

Workup

  1. temperatureThen, the solution is cooled in an ice bath
  2. stirringAfter stirring for 5 min
  3. concentrationthe resulting mixture is concentrated
  4. customthe residue is purified by HPLC on reversed phase (MeCN/H2O/NH3)

Sources & evidence

ORD record
ord-2a8e8a34d44e4b7188c439878f67676c
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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