Sodium borohydride → HCID 71556956, compound

HRID 1411592Notes

Reaction equation

HRID 1411592 reaction equation
[F:1][C:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]2[CH2:11][CH2:12][N:13]([C:16]3[N:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:29]=[C:28]([NH:30][C:31]5[CH:36]=[CH:35][C:34]([N:37]6[CH2:42][CH2:41][N:40]([CH:43]7[CH2:46][O:45][CH2:44]7)[CH2:39][C@@H:38]6[CH3:47])=[CH:33][N:32]=5)[C:27](=[O:48])[N:26]([CH3:49])[CH:25]=4)[C:17]=3[CH:18]=[O:19])[C:14](=[O:15])[C:3]=12.[BH4-].[Na+]>CO>[F:1][C:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]2[CH2:11][CH2:12][N:13]([C:16]3[C:17]([CH2:18][OH:19])=[C:20]([C:24]4[CH:29]=[C:28]([NH:30][C:31]5[CH:36]=[CH:35][C:34]([N:37]6[CH2:42][CH2:41][N:40]([CH:43]7[CH2:44][O:45][CH2:46]7)[CH2:39][C@@H:38]6[CH3:47])=[CH:33][N:32]=5)[C:27](=[O:48])[N:26]([CH3:49])[CH:25]=4)[CH:21]=[CH:22][N:23]=3)[C:14](=[O:15])[C:3]=12

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86684242HCID 86684242, compound

Product 1

HCID 71556956HCID 71556956, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 25 mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 136a (100 mg, 1.0 eq., 0.15 mmol), NaBH4(17 mg, 3.0 eq., 0.45 mmol), and MeOH (10 mL). The mixture was stirred at room temperature for 1 h. The residue was purified by reverse-phase prep-HPLC to afford 136 (64 mg, 64%). LCMS: [M+H]+ 669.3. 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J=2.0, 1H), 8.48 (d, J=5.0, 1H), 7.96 (d, J=2.5, 1H), 7.83-7.82 (m, 2H), 7.36 (d, J=5.0, 1H), 7.30 (dd, J=2.5, 9.0, 1H), 6.81 (d, J=8.5, 1H), 4.99-4.96 (m, 1H), 4.71-4.61 (m, 5H), 4.45-3.83 (m, 5H), 3.71 (s, 3H), 3.54-3.45 (m, 2H), 3.08-3.06 (m, 2H), 2.56-2.47 (m, 7H), 2.21-2.17 (m, 1H), 1.89-1.76 (m, 4H), 0.98 (d, J=6.5, 3H)

Workup

  1. customA 25 mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customThe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-0c30c3ee6e4343bd8c1603ec62e2cdb2
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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