Hydrochloric Acid → HCID 10872075, compound

HRID 2269593Notes

Reaction equation

HRID 2269593 reaction equation
O.[OH-].[Li+].[NH:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:5][C:6]([N:8]([CH2:10][C:11]([N:13]([CH3:22])[C@H:14]([C:18]([O:20]C)=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:9])=[O:7].Cl>C1COCC1.CO.O>[NH:4]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:5][C:6]([N:8]([CH2:10][C:11]([N:13]([CH3:22])[C@H:14]([C:18]([OH:20])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 15280902HCID 15280902, compound

Product 1

HCID 10872075HCID 10872075, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

From 600; Lithium hydroxide monohydrate (249 mg, 5.9 mmol) was added to a solution of 600 (740 mg, 1.98 mmol) in 15 mL of THF—CH3OH—H2O (3:1:1) at 25° C. and the resulting reaction mixture was stirred for 3 h. The reaction mixture was poured onto 3M aqueous HCl (8 mL) and extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo to give 7 (638 mg, 712 mg theoretical, 90%) as a white solid which was employed directly in the next reaction without further purification: white foam, mp 57-60° C.; 1H NMR (CDCl3, 400 MHz) 5.67 and 5.58 (two s, 1H), 4.63 (d, 1H, J=10.4 Hz), CH), 4.10-3.82 (m, 4H), 3.05, 3.04, 3.01 and 2.88 (four s, 6H), 2.30-2.20 (m, 1H), 1.43 and 1.41 (two s, 9H), 1.04 and 0.88 (two d, 6H, J=6.7 Hz); IR (KBr)max 3421, 2974, 1706, 1656, 1495, 1419, 1367, 1292, 1250, 1171, 1053, 953, 870, 837, 670 cm−1.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give 7 (638 mg, 712 mg theoretical, 90%) as a white solid which
  7. customwas employed directly in the next reaction without further purification

Sources & evidence

ORD record
ord-eb7c1efd0602411985bc8e292094ae40
Source dataset
uspto-grants-2001_12
Patent number
US06329497B1

Reaction notes

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