Aluminium lithium hydride → HCID 53709763, compound

HRID 1387129Notes

Reaction equation

HRID 1387129 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:26][CH:25]=2)=[CH:10][CH:9]=1)[NH2:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:5][C@H:4]([CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:28][CH:29]=2)=[CH:12][CH:13]=1)[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70186562HCID 70186562, compound

Product 1

HCID 53709763HCID 53709763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

O-[4-[3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl ester in THF (4 mL) was treated with lithium aluminum hydride (22 mg) at ambient temperature under argon for 5 h. The reaction was quenched with water (0.5 mL) and sodium hydroxide solution (1.0 M, 1 mL) and stirred for 10 more min. before it was concentrated under reduced pressure. The residue was extracted with dichloromethane (20 mL×3) from brine (30 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:10:85) followed by NH4OH:MeOH:EtOAc (5:10:85) afforded the product (27 mg).

Workup

  1. customThe reaction was quenched with water (0.5 mL) and sodium hydroxide solution (1.0 M, 1 mL)
  2. concentrationbefore it was concentrated under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (20 mL×3) from brine (30 mL)
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8575666e3ba4439e9b10f3b876d8d0b5
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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