Water → HCID 67322718, compound

HRID 1401791Notes

Reaction equation

HRID 1401791 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH:11]([NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][CH:28]=[C:29]([C:31]3[CH:40]=[CH:39][C:38]4[C:37]([CH3:42])([CH3:41])[CH2:36][CH2:35][C:34]([CH3:44])([CH3:43])[C:33]=4[CH:32]=3)[N:30]=2)[CH2:22][CH2:21]1)[CH2:12][CH2:13][C:14](OCC)=[O:15])C.O>C1COCC1>[CH3:41][C:37]1([CH3:42])[CH2:36][CH2:35][C:34]([CH3:43])([CH3:44])[C:33]2[CH:32]=[C:31]([C:29]3[N:30]=[C:26]([N:23]4[CH2:24][CH2:25][CH:20]([NH:19][CH:11]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:10][OH:9])[CH2:21][CH2:22]4)[S:27][CH:28]=3)[CH:40]=[CH:39][C:38]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67323736HCID 67323736, compound

Product 1

HCID 67322718HCID 67322718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.3 mg (0.11 mmol) of lithium aluminium hydride were initially introduced in 2 ml of THF, and 21 mg (0.04 mmol) of 2-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}pentanedioic acid diethyl ester from step a, pre-dissolved in 2 ml of THF, were slowly added. The reaction mixture was stirred at room temperature overnight, 20 ml of water were added, and the mixture was extracted twice with EA. The organic phase was dried over sodium sulfate, filtered, stripped off to dryness and purified by means of preparative HPLC. The product is in the form of the TFA salt.

Workup

  1. additionwere slowly added
  2. extractionthe mixture was extracted twice with EA
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-1ef19d832fc544e09c4eead0a0cfda74
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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