Lithium Hydroxide → HCID 68864887, compound

HRID 1726012Notes

Reaction equation

HRID 1726012 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([NH:18][C:19]2[CH:28]=[CH:27][C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:20]=2[C:29]([O:31]C)=[O:30])(=[O:17])=[O:16])[CH2:3][CH2:2]1.[CH2:33]([CH:35]([CH2:38][CH3:39])[CH:36]=O)[CH3:34].C([BH3-])#N.[Li+].[OH-]>CN(C=O)C.C(O)(=O)C>[CH2:33]([CH:35]([CH2:38][CH3:39])[CH2:36][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([NH:18][C:19]2[CH:28]=[CH:27][C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:20]=2[C:29]([OH:31])=[O:30])(=[O:17])=[O:16])[CH2:3][CH2:2]1)[CH3:34]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 73592-EthylbutyraldehydeHCID 498716Cyano-borohydrideHCID 11719508HCID 11719508, compound

Product 1

HCID 68864887HCID 68864887, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of Example 557B (0.026 g, 0.06 mmol) in DMF (2.5 mL) was treated with acetic acid (0.01 mL) and 2-ethylbutanal (0.025 g, 0.06 mmol). The mixture was shaken at 50° C. for 20 minutes, treated with macroporous polystyrene bound cyanoborohydride resin (85 mg, 0.2 mmol), shaken at 70° C. for 5 hours, and filtered. The filtrate was concentrated, dissolved in 1 mL 2:1 dioxane water, treated with LiOH (25 mg, 0.6 mmol) and heated to 160° C. for 30 minutes in a microwave reactor. The reaction mixture was concentrated and the residues purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (6.5 mg). MS (ESI(+)) m/e 528 (M+H)+; (ESI(−)) m/e 526 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.51 (dd, 1H), 7.38 (dt, 1H), 6.94 (d, 1H), 6.84 (d, 1H), 6.62 (m, 2H), 6.07 (m, 1H), 3.13 (m, 2H), 2.95-2.80, (m, 4H), 2.66 (m, 4H), 1.83 (m, 3H), 1.66 (m, 5H), 1.34 (m, 6H), 0.85 (t, 6H).

Workup

  1. stirringshaken at 70° C. for 5 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in 1 mL 2:1 dioxane water
  5. temperatureheated to 160° C. for 30 minutes in a microwave reactor
  6. concentrationThe reaction mixture was concentrated
  7. customthe residues purified by C18 reverse-phase

Sources & evidence

ORD record
ord-b429f45cf1c942f2a6c14fdb05a25971
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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