Hydrochloric Acid → HCID 68855968, compound

HRID 1782751Notes

Reaction equation

HRID 1782751 reaction equation
C([BH3-])#[N:2].[Na+].[NH2:5][C:6]1[C:38]([Br:39])=[CH:37][C:9]([CH2:10][C@H:11]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([CH:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH2:26][CH2:25]2)=[O:23])[NH:12][C:13]([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)=[O:14])=[CH:8][C:7]=1[Br:40].C([O-])(=O)C.[NH4+].Cl>CO>[NH2:5][C:6]1[C:38]([Br:39])=[CH:37][C:9]([CH2:10][C@H:11]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([CH:30]3[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[CH2:26][CH2:25]2)=[O:23])[NH:12][C:13]([N:15]2[CH2:20][CH2:19][CH:18]([NH2:2])[CH2:17][CH2:16]2)=[O:14])=[CH:8][C:7]=1[Br:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 54104317HCID 54104317, compound

Product 1

HCID 68855968HCID 68855968, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

653 mg (10.4 mMol) 95% sodium cyanoborohydride (Aldrich 15.615-9) was stirred into the mixture of 930 mg (1.48 mMol) 1-[4-amino-3,5-dibromo-N-[(4-oxo-1-piperidinyl)carbonyl]-D-phenylalanyl]-4-(1-methyl-4-piperidinyl)-piperidine, 1143 mg (14.8 mMol) ammonium acetate (Merck No. 1115) and 30 ml anhydrous methanol at room temperature, and was stirred overnight. The deposit was adjusted to pH ≦2 with conc. hydrochloric acid and was evaporated in a vacuum. The residue is taken up in water and made alkaline with 40% soda lye. Exhaustive extraction with dichloromethane followed, then the combined extracts were dried over sodium sulphate and evaporated in a vacuum. The residue was purified over 100 g silica gel (Amicon, 35-70 μm) by column chromatography using dichloromethane/methanol/conc. ammonia(60/40/5 v/v/v) for elution. From the suitable fractions, 250 mg (27% of theory) of the sought substance was isolated as a colourless, amorphous product of Rf 0.15 (dichloromethane/methanol/conc. ammonia 50/50/0.5 v/v/v).

Workup

  1. customwas evaporated in a vacuum
  2. extractionExhaustive extraction with dichloromethane
  3. dry with materialthe combined extracts were dried over sodium sulphate
  4. customevaporated in a vacuum
  5. customThe residue was purified over 100 g silica gel (Amicon, 35-70 μm) by column chromatography
  6. washammonia(60/40/5 v/v/v) for elution
  7. customFrom the suitable fractions, 250 mg (27% of theory) of the sought substance was isolated as a colourless, amorphous product of Rf 0.15 (dichloromethane/methanol/conc. ammonia 50/50/0.5 v/v/v)

Sources & evidence

ORD record
ord-8d5284a1679a4cf5a3b8e581bbff6cba
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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