Acetic Acid → HCID 136342239, compound

HRID 1611441Notes

Reaction equation

HRID 1611441 reaction equation
CC(C)C([O:5][C@@H:6]1[C@@H:10]([CH2:11][O:12]C(=O)C(C)C)[O:9][C@@H:8]([N:18]2[C:22]3[N:23]=[C:24]([NH:29]C=O)[N:25]=[C:26]([O:27]C)[C:21]=3[C:20]([Cl:32])=[C:19]2[Cl:33])[CH2:7]1)=O.CC(O)=O>[OH-].[Na+]>[NH2:29][C:24]1[NH:25][C:26](=[O:27])[C:21]2[C:20]([Cl:32])=[C:19]([Cl:33])[N:18]([C@@H:8]3[O:9][C@H:10]([CH2:11][OH:12])[C@@H:6]([OH:5])[CH2:7]3)[C:22]=2[N:23]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 88180221HCID 88180221, compound

Product 1

HCID 136342239HCID 136342239, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of compound (49) (200 mg, 0.4 mmol) in 2N aq. NaOH (8 ml) is boiled under reflux for 3 h. After the solution has been neutralized with conc. AcOH, the reaction product is filtered, washed with water and dried. Colorless crystals (128 mg, 96%) are obtained after crystallizing from CH3CN. 1H-NMR ([D6] DMSO): δ=2.22 (m, Hα—C(2′)), 2.92 (m, Hβ—C(2′)), 3.52 (m, H—C(5′)), 3.72 (m, H—C(4′)), 4.33 (m, H—C(3′)), 4.81 (t, 5′-OH), 5.22 (d, 3′-OH), 6.35 (dd, H—C(1′)), 6.46 (br., NH2), 10.75 (s, NH).

Workup

  1. temperatureunder reflux for 3 h
  2. filtrationthe reaction product is filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a6215332ccb443f9afcf8b8b21002574
Source dataset
uspto-grants-2006_01
Patent number
US06987177B2

Reaction notes

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