Sodium cyanoborohydride → HCID 117831216, compound

HRID 518935Notes

Reaction equation

HRID 518935 reaction equation
C([BH3-])#N.[Na+].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:59]2[CH:60]=[C:61]3[CH:67]=[CH:66][N:65]([CH3:68])[C:62]3=[N:63][CH:64]=2)[C:13]([C:15]2[CH:16]=[C:17]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32](=[O:39])[N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:26][C:25]=3[C:40]([N:42]3[C@H:51]([CH2:52][N:53]4[CH2:58][CH2:57][O:56][CH2:55][CH2:54]4)[CH2:50][C:49]4[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=4)[CH2:43]3)=[O:41])[N:18]3[C:23]=2[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:14])=[CH:8][CH:7]=1>C(O)(=O)C>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([C:59]2[CH:60]=[C:61]3[CH2:67][CH2:66][N:65]([CH3:68])[C:62]3=[N:63][CH:64]=2)[C:13]([C:15]2[CH:16]=[C:17]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32](=[O:39])[N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:26][C:25]=3[C:40]([N:42]3[C@H:51]([CH2:52][N:53]4[CH2:58][CH2:57][O:56][CH2:55][CH2:54]4)[CH2:50][C:49]4[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=4)[CH2:43]3)=[O:41])[N:18]3[C:23]=2[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:14])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydride3×HCID 117831128HCID 117831128, compound

Product 1

HCID 117831216HCID 117831216, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.71 g (11 mmol) of sodium cyanoborohydride is added to a solution, in 20 mL of acetic acid, of the compound obtained in Step F (2.0 g, 2.2 mmol). After stirring for 14 hours at ambient temperature, 0.36 g (5.5 mmol) of sodium cyanoborohydride is again added, and then the reaction mixture is heated at 50° C. for 3 hours before a second addition of 0.1 eq. of sodium cyanoborohydride to complete the reaction in 30 minutes at 50° C. The acetic acid is evaporated off under reduced pressure, and then the residue is taken up in dichloromethane and washed with saturated aqueous NaHCO3 solution, water and brine. The combined aqueous phases are extracted with dichloromethane. The resulting organic phases are dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product obtained is purified by chromatography over silica gel (dichloromethane/ethanol/ammonia gradient) to yield the title compound in the form of a meringue.

Workup

  1. customthe reaction in 30 minutes at 50° C
  2. customThe acetic acid is evaporated off under reduced pressure
  3. washwashed with saturated aqueous NaHCO3 solution, water and brine
  4. extractionThe combined aqueous phases are extracted with dichloromethane
  5. dry with materialThe resulting organic phases are dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product obtained
  9. customis purified by chromatography over silica gel (dichloromethane/ethanol/ammonia gradient)

Sources & evidence

ORD record
ord-f232dac05df94538ad2de7eca804f59e
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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