Hydrochloric Acid → HCID 57224288, compound

HRID 1386917Notes

Reaction equation

HRID 1386917 reaction equation
CC([O:5][C:6]([C@@H:8]1[CH2:24][S:23][S:22][CH2:21][C@H:20]([NH:25]C([C@@H]2[C@@H](C3C=CC(O)=CC=3)CCN2C(=O)C)=O)[C:19](=[O:43])[NH:18][CH2:17][CH2:16][C:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10](=[O:44])[NH:9]1)=[O:7])(C)C.Cl>ClCCl.O1CCOCC1>[NH2:25][C@@H:20]1[C:19](=[O:43])[NH:18][CH2:17][CH2:16][C:11]2([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:44])[NH:9][C@H:8]([C:6]([OH:7])=[O:5])[CH2:24][S:23][S:22][CH2:21]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131722817HCID 131722817, compound

Product 1

HCID 57224288HCID 57224288, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of this ester (3.01 g) in 15 mL of dry dichloromethane was added 4N HCl in dioxane (50 mL) in one portion at room temperature. The resulting solution was stirred at room temperature for 4.5 hours to give a suspension. The suspension was diluted with 50 mL of mixed solvent (3:7 dichloromethane:ether) and was filtered. The light yellow filter-cake was washed with above mixed solvent (2×20 mL) followed by ether (2×20 mL). The cake was dried under vacuum to give a light yellow powder (2.51 g, HLPC purity: >85%). The final purification was effected with RP-HPLC to give (8R,13R)-13-amino-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylic acid as a white solid (1.55 g, 2.61 mmol) in 52 % yield. HRMS (M+H) Obs. 593.209, Calcd. 593.2103.

Workup

  1. customto give a suspension
  2. filtrationwas filtered
  3. filtrationThe light yellow filter-cake
  4. washwas washed with
  5. additionabove mixed solvent (2×20 mL)
  6. customThe cake was dried under vacuum
  7. customto give a light yellow powder (2.51 g, HLPC purity: >85%)
  8. customThe final purification

Sources & evidence

ORD record
ord-99a4ed296dfe489a8167d685c58707a3
Source dataset
uspto-grants-2001_07
Patent number
US06265572B1

Reaction notes

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