Hydrochloric Acid → HCID 86726340, compound

HRID 629741Notes

Reaction equation

HRID 629741 reaction equation
[ClH:1].C(OC([NH:9][C@H:10]([C:26]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1[CH2:36][CH2:37][C@H:38]1[O:43][CH2:42][C@@H:41]([CH2:44][O:45][C:46](=[O:53])[NH:47][CH2:48][C:49]([F:52])([F:51])[F:50])[N:40](C(OC(C)(C)C)=O)[CH2:39]1)=[O:27])[CH:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[ClH:1].[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C@@H:10]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=2[CH2:36][CH2:37][C@H:38]2[O:43][CH2:42][C@@H:41]([CH2:44][O:45][C:46](=[O:53])[NH:47][CH2:48][C:49]([F:52])([F:51])[F:50])[NH:40][CH2:39]2)=[O:27])[NH2:9])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86726341HCID 86726341, compound

Product 1

HCID 86726340HCID 86726340, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl (44.5 mL, 178 mmol) in dioxane was added to a solution of tert-Butyl (2R,5S)-2-[2-(2-{[N-(tert-butoxycarbonyl)-4-fluoro-β-(4-fluorophenyl)-L-phenylalanyl]amino}-6-fluorophenyl)ethyl]-5-({[(2,2,2-trifluoroethyl)carbamoyl]oxy}methyl)morpholine-4-carboxylate (7.46 g, 8.89 mmol) in Dioxane (89 mL) at 0° C. and then the reaction was stirred at rt for 4 hours. The solvent was removed in vacuo and ether was added to the residue to afford a white ppt. The ppt was triturated with ether (×3) and the residing white solid dried under high vacuum to afford the title compound (5.84 g, 8.21 mmol, 92% yield) as a white powder, MS (ESI): m/z=639.5 (MH+); 100% pure by LCMS.

Workup

  1. customThe solvent was removed in vacuo and ether
  2. additionwas added to the residue
  3. customto afford a white ppt
  4. customThe ppt was triturated with ether (×3)
  5. customthe residing white solid dried under high vacuum

Sources & evidence

ORD record
ord-30430bbfaec74d379743bcb1a87cbb99
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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