Lithium Hydroxide → HCID 68864593, compound

HRID 1725993Notes

Reaction equation

HRID 1725993 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[C:6]=1[NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[O:4].[Li+].[OH-]>O.O1CCOCC1>[C:17](/[CH:16]=[CH:15]/[C:7]1[C:6]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[C:5]([C:3]([OH:4])=[O:2])[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68866001HCID 68866001, compound

Product 1

HCID 68864593HCID 68864593, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
160 °C

Procedure

A solution of Example 476D (20 mg, 0.05 mmol) in 0.5 mL of 2:1 dioxane water was treated with LiOH (13 mg, 0.3 mmol) and heated to 160° C. for 27.5 minutes in a microwave reactor. The reaction mixture was concentrated and the residue was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (DCI) m/e 419 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 12.92 (br s, 1H), 12.11 (br s, 1H), 9.69 (br s, 1H), 7.60 (m, 2H), 7.54 (m, 1H), 7.49-7.42 (m, 4H), 6.13 (d, 1H), 2.75 (m, 2H), 2.67 (m, 2H), 1.70 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by C18 reverse-phase

Sources & evidence

ORD record
ord-559c5fafc797419197209edfb111d69a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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