Hydrochloric Acid → HCID 86687886, compound

HRID 1022524Notes

Reaction equation

HRID 1022524 reaction equation
[CH3:1][NH:2][C@H:3]([C:7]([NH:9][C@H:10]([C:14]([N:16]([C@@H:18]([C@@H:54]([CH3:57])[CH2:55][CH3:56])[C@H:19]([O:52][CH3:53])[CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C@H:28]([O:50][CH3:51])[C@@H:29]([CH3:49])[C:30]([NH:32][C@@H:33]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34]([N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][O:37]1)=[O:35])=[O:31])=[O:22])[CH3:17])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:8])[C@@H:4]([CH3:6])[OH:5].C=O.[C:60]([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:60])[C@H:3]([C:7]([NH:9][C@H:10]([C:14]([N:16]([C@@H:18]([C@@H:54]([CH3:57])[CH2:55][CH3:56])[C@H:19]([O:52][CH3:53])[CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C@H:28]([O:50][CH3:51])[C@@H:29]([CH3:49])[C:30]([NH:32][C@@H:33]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34]([N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][O:37]1)=[O:35])=[O:31])=[O:22])[CH3:17])=[O:15])[CH:11]([CH3:13])[CH3:12])=[O:8])[C@@H:4]([CH3:6])[OH:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86687887HCID 86687887, compound

Product 1

HCID 86687886HCID 86687886, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

84 mg (0.105 mmol) of N-methyl-L-threonyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]amino}-3-oxopropyl]-pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Example 19) were taken up in 5 ml of dioxane/water (1:1), and 31 μl (0.418 mmol) of a 37% strength aqueous formaldehyde solution and 8 mg (0.126 mmol) of sodium cyanoborohydride were added. Using 1 ml of 0.1 N hydrochloric acid, the mixture was then adjusted to pH 6-7 and stirred at 100° C. for 1 h. The reaction was then poured into a mixture of semisaturated aqueous sodium bicarbonate solution and ethyl acetate. The organic phase was separated off, washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue was finally lyophilized from acetonitrile/water. This gave 72 mg (84% of theory) of the title compound in the form of a colourless foam.

Workup

  1. customThe organic phase was separated off
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-518ec87627f744348ff7381e7671321e
Source dataset
uspto-grants-2014_05
Patent number
US08722629B2

Reaction notes

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