Hydrochloric Acid → HCID 21844867, compound

HRID 618915Notes

Reaction equation

HRID 618915 reaction equation
C([N:3]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:11][CH2:10][N:9]([CH:23]([CH:30]([N:37]2[CH2:48][CH2:47][N:46]([CH2:49][C:50]([O:52]C(C)(C)C)=[O:51])[CH2:45][CH2:44][N:43](C=O)[CH2:42][CH2:41][N:40]([CH2:59][C:60]([O:62]C(C)(C)C)=[O:61])[CH2:39][CH2:38]2)[C:31]([O:33]C(C)C)=[O:32])[C:24]([O:26]C(C)C)=[O:25])[CH2:8][CH2:7][N:6]([CH2:67][C:68]([O:70]C(C)(C)C)=[O:69])[CH2:5][CH2:4]1)=O.O.[Li+].[OH-].Cl>C(O)C>[C:16]([CH2:15][N:12]1[CH2:13][CH2:14][NH:3][CH2:4][CH2:5][N:6]([CH2:67][C:68]([OH:70])=[O:69])[CH2:7][CH2:8][N:9]([CH:23]([CH:30]([N:37]2[CH2:38][CH2:39][N:40]([CH2:59][C:60]([OH:62])=[O:61])[CH2:41][CH2:42][NH:43][CH2:44][CH2:45][N:46]([CH2:49][C:50]([OH:52])=[O:51])[CH2:47][CH2:48]2)[C:31]([OH:33])=[O:32])[C:24]([OH:26])=[O:25])[CH2:10][CH2:11]1)([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 88278010HCID 88278010, compound

Product 1

HCID 21844867HCID 21844867, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

In a 250 mL RB flask, the compound of Example 13 (1.0 g, 1.5 mmol) is dissolved in ethanol (30 mL) and water is added until the solution turns slightly turbid. The reaction mixture is heated at 100° C. and 1N LiOH (12 mL) is added. After maintaining the mixture at 100° C. for 8 hours, the solution is adjusted to pH 0.5 with 5N HCl (aq), and the mixture is refluxed for 1.5 hours and stirred at ambient temperature for an additional 18 hours. The cooled reaction material is desalted by ion exchange chromatography using an AG5OW-X8 [80 mL, (H+ form)] strongly cation exchange resin. The product is eluted with 1.0N NH4OH. The fractions containing product are combined and concentrated to afford the title compound.

Workup

  1. temperatureAfter maintaining the mixture at 100° C. for 8 hours
  2. temperaturethe mixture is refluxed for 1.5 hours
  3. customThe cooled reaction material
  4. washThe product is eluted with 1.0N NH4OH
  5. additionThe fractions containing product
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-36f0f8a3a3ce4afea5becf6949c09f86
Source dataset
uspto-grants-1999_09
Patent number
US05958373

Reaction notes

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