Hydrochloric Acid → HCID 15942505, compound

HRID 2360644Notes

Reaction equation

HRID 2360644 reaction equation
[CH:1]1([O:6][C:7](=[O:43])[C@H:8]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:41])[NH:32][O:33]C(OCC(C)C)C)=[CH:19][CH:18]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C(Cl)Cl.O1CCOCC1>[CH:1]1([O:6][C:7](=[O:43])[C@H:8]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:41])[NH:32][OH:33])=[CH:21][CH:22]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57971646HCID 57971646, compound

Product 1

HCID 15942505HCID 15942505, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-{4-[7-(1-Isobutoxy-ethoxycarbamoyl)-heptanoylamino]-benzylamino}-phenyl-acetic acid cyclopentyl ester (50 mg, 0.08 mmol, 1 eq) was dissolved in DCM (0.5 mL) and stirred with 4M HCl in dioxane (0.2 mL) for 30 min. The resulting salt was concentrated, dissolved in methanol and purified by preparative HPLC to yield compound (83). LCMS purity 94%, m/z 496 [M++H]+, 1H NMR (300 MHz, MeOD), δ: 1.41-1.95 (16H, m, 8×CH2), 2.15-2.17 (2H, m, CH2), 2.40 (2H, t, J=7.2 Hz, CH2), 4.16 (2H, q, J=13.5 Hz, CH2), 5.12 (1H, s, CH), 5.27-5.30 (1H, m, CH), 7.40 (2H, d, J=8.7 Hz, Ar—H), 7.50-7.56 (5H, m, Ar—H), 7.67 (2H, d, J=8.7 Hz, Ar—H).

Workup

  1. concentrationThe resulting salt was concentrated
  2. dissolutiondissolved in methanol
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c3c6d053111a4d829526dce390f3322b
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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