Sodium borohydride → HCID 70823096, compound

HRID 389224Notes

Reaction equation

HRID 389224 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@:10]23[NH:50][C:49](=[O:51])[C@@H:48]4[CH2:52][C@@H:45]5[CH2:46][N:47]4[C:53](=[O:54])[C@@H:20]([NH:21][C:22](=[O:55])[O:23][C@H:24]4[C@H:28]([CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][C:34]6[C:43]([O:44]5)=[CH:42][C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:35]=6)[CH2:27][CH2:26][CH2:25]4)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=[CH:13][C@@H:12]2[CH2:11]3)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[BH4-].[Na+]>CCO>[CH:1]1([S:4]([NH:7][C:8]([C@:10]23[NH:50][C:49](=[O:51])[C@@H:48]4[CH2:52][C@@H:45]5[CH2:46][N:47]4[C:53](=[O:54])[C@@H:20]([NH:21][C:22](=[O:55])[O:23][C@H:24]4[C@H:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]6[C:43]([O:44]5)=[CH:42][C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:35]=6)[CH2:27][CH2:26][CH2:25]4)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=[CH:13][C@@H:12]2[CH2:11]3)=[O:9])(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59571164HCID 59571164, compound

Product 1

HCID 70823096HCID 70823096, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a 0° C. solution of the compound from Step 6 (26 mg, 0.034 mmol) in EtOH (20 mL) was added BiCl3 (154 mg, 0.487 mmol) and then NaBH4 (363 mg, 9.61 mmol). The mixture was then warmed to 40° C. for 15 minutes. The black solids were then filtered off and washed with EtOH. 1N HCl was then added to quench the mixture at 0° C.; the EtOH was then removed in vacuo; and the pH was adjusted to ˜4. The mixture was then extracted with EtOAc (2×), dried over MgSO4, and the solvent was removed in vacuo to yield crude material which was purified by reverse phase chromatography using a 0-100% CH3CN/0.15% aqueous trifluoracetic acid gradient to yield the title compound. 1H NMR (500 MHz) (CD3OD) δ 8.99 (s, 1H), 8.56 (s, 1H), 8.15 (d, J=8.0 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.92 (app. t, J=7.2 Hz, 1H), 7.83 (app. t, J=7.6 Hz, 1H), 5.68 (q, J=10.0 Hz, 1H), 5.61 (app. t, J=3.2 Hz, 1H), 5.05 (app. t, J=8.8 Hz, 1H), 4.95-4.47 (m, 2H), 4.51 (dd, J=10.2 Hz, 6.8 Hz, 1H), 4.30 (d, J=10.4 Hz, 1H), 4.14 (dd, J=11.8 Hz, 3.6 Hz, 1H), 3.17 (m, 2H), 2.85 (m, 1H), 2.65 (m, 2H), 2.53 (m, 1H), 2.45 (q, J=8.4 Hz, 1H), 2.0-1.8 (m, 5H), 1.8-1.2 (m, 21H), 1.2-0.9 (m, 4H). LRMS ESI+ (M+H) 776.1, calcd for C41H54N5O8S: 776.3.

Workup

  1. filtrationThe black solids were then filtered off
  2. washwashed with EtOH
  3. addition1N HCl was then added
  4. customto quench the mixture at 0° C.
  5. customthe EtOH was then removed in vacuo
  6. extractionThe mixture was then extracted with EtOAc (2×)
  7. dry with materialdried over MgSO4
  8. customthe solvent was removed in vacuo
  9. customto yield crude material which
  10. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-321667c50ce144e5aa8ea2797e0f052b
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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