Formaldehyde → HCID 117598928, compound

HRID 522402Notes

Reaction equation

HRID 522402 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][O:6][C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]3[O:17][C@H:18]4[CH2:41][N:21]([C:22](=[O:40])[C@H:23]([C:36]([CH3:39])([CH3:38])[CH3:37])[NH:24][C:25](=[O:35])[O:26][C@@H:27]5[CH2:34][C@H:28]5[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:8]=23)[C@H:20]([C:42]([NH:44][C@:45]2([C:50](=[O:59])[NH:51][S:52]([C:55]3([CH3:58])[CH2:57][CH2:56]3)(=[O:54])=[O:53])[CH2:47][C@H:46]2[CH:48]=[CH2:49])=[O:43])[CH2:19]4)[CH2:2]1.[CH2:60]=O.[BH4-].[Na+]>CO>[C:36]([C@H:23]1[C:22](=[O:40])[N:21]2[CH2:41][C@@H:18]([CH2:19][C@H:20]2[C:42]([NH:44][C@:45]2([C:50](=[O:59])[NH:51][S:52]([C:55]3([CH3:58])[CH2:56][CH2:57]3)(=[O:54])=[O:53])[CH2:47][C@H:46]2[CH:48]=[CH2:49])=[O:43])[O:17][C:9]2=[N:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:7]([O:6][CH2:5][CH:3]3[CH2:2][N:1]([CH3:60])[CH2:4]3)=[C:8]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]2[CH2:34][C@H:27]2[O:26][C:25](=[O:35])[NH:24]1)([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 117598989HCID 117598989, compound

Product 1

HCID 117598928HCID 117598928, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of the amine from Step 1 (20.6 mg) in methanol (1 mL) was added formaldehyde (10 μl). Sodium borohydride (5.6 mg) was added slowly. The clear reaction mixture was stirred overnight at room temperature. The solvent was removed in vacuo and the product was dissolved in ethyl acetate and water (with acetic acid to a pH=5). The mixture was extracted (3×) with ethyl acetate. The combined organics were dried with sodium sulfate, filtered and concentrated. Purification by flash chromatography (ISCO reverse phase, 0 to 95% water in acetonitrile followed by ISCO: 0 to 20% methanol in DCM) gave the desired product (1.4 mg). LRMS (ES+) m/z 849.55 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe product was dissolved in ethyl acetate
  3. extractionThe mixture was extracted (3×) with ethyl acetate
  4. dry with materialThe combined organics were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (ISCO reverse phase, 0 to 95% water in acetonitrile followed by ISCO: 0 to 20% methanol in DCM)

Sources & evidence

ORD record
ord-8f1ef88962094759a79fdfc18066a161
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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