Lithium borohydride → HCID 10272575, compound

HRID 719208Notes

Reaction equation

HRID 719208 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:9][C:10]([C:12]1[C:25]2[C:16](=[N:17][C:18]3[C:23]([N:24]=2)=[C:22]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:21]2=[CH:20][CH:19]=3)[CH:15]=[CH:14][CH:13]=1)=[O:11])[CH2:5][N:6]([CH3:8])[CH3:7].[BH4-].[Li+]>O1CCCC1.C(O)(C)C>[CH3:7][N:6]([CH3:8])[CH2:5][CH:4]([NH:9][C:10]([C:12]1[C:25]2[C:16](=[N:17][C:18]3[C:23]([N:24]=2)=[C:22]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:21]2=[CH:20][CH:19]=3)[CH:15]=[CH:14][CH:13]=1)=[O:11])[CH2:3][OH:2]

Participants

5

Reactant 2

HCID 4148881Lithium borohydride2×HCID 10119896HCID 10119896, compound

Product 1

HCID 10272575HCID 10272575, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-dimethylamino-2-[(4-methoxy-benzo[a]phenazine-11-carbonyl)-amino]-propionic acid methyl ester (335 mg) and lithium borohydride (72 mg) in tetrahydrofuran (10 mL) and isopropanol (10 mL) was stirred at room temperature for 18 hours. Another 5 equivalents of lithium borohydride were added and the mixture stirred for another 18 hours. The reaction was quenched with ammonium chloride solution and extracted with ethyl acetate, dried (MgSO4) and the solvent removed in vacuo to yield a brown gum. Purification using flash chromatography and trituration with ether yielded the desired title compound as an orange powder.

Workup

  1. stirringthe mixture stirred for another 18 hours
  2. customThe reaction was quenched with ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto yield a brown gum
  7. customPurification

Sources & evidence

ORD record
ord-2172ada527614d03a4e3f5e6b29d9bfe
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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