Sodium borohydride → HCID 59485822, compound

HRID 1972271Notes

Reaction equation

HRID 1972271 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@H:11]([CH2:21][N:22]3[N:26]=[N:25][C:24]([CH2:27][C:28](OCC)=[O:29])=[N:23]3)[O:10][C:9]2=[O:33])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@H:11]([CH2:21][N:22]3[N:26]=[N:25][C:24]([CH2:27][CH2:28][OH:29])=[N:23]3)[O:10][C:9]2=[O:33])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59485815HCID 59485815, compound

Product 1

HCID 59485822HCID 59485822, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(2-(((4S,5S)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-2-oxooxazolidin-5-yl)methyl)-2H-tetrazol-5-yl)acetate (50 mg, 0.11 mmol) [Example 379] in MeOH (1 mL) is treated with excess sodium borohydride at room temperature for 30 min. The reaction is quenched with 1 mL 0.1 M HCl and extracted with EtOAc (3×5 mL). The combined organics are dried over MgSO4, filtered and concentrated to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 7.47-7.43 (m, 2H), 7.33-7.29 (m, 3H), 7.04 (app t, J=2.0 Hz, 1H), 7.00-6.98 (app d, J=7.7 Hz, 1H), 6.90 (ddd, J=8.3, 2.6, 0.9 Hz, 1H), 5.60 (d, J=5.2 Hz, 1H), 5.33 (dd, J=14.6, 6.2 Hz, 1H), 5.25 (dd, J=14.6, 4.1 Hz, 1H), 4.99 (ddd, J=6.2, 5.2, 4.1 Hz, 1H), 3.89-3.76 (m, 6H), 2.99 (t, J=6.3 Hz, 2H), HPLC-MS calculated C20H20ClN5O4 (M+H+) 430.1, found 430.1.

Workup

  1. customThe reaction is quenched with 1 mL 0.1 M HCl
  2. extractionextracted with EtOAc (3×5 mL)
  3. dry with materialThe combined organics are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b18f2446b1b44fa398c98d4b7b204104
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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