Hydrochloric Acid → HCID 15942505, compound

HRID 548247Notes

Reaction equation

HRID 548247 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-861a64081da44dd68ac78373f50d8aef
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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