Hydrochloric Acid → HCID 86611240, compound

HRID 1171971Notes

Reaction equation

HRID 1171971 reaction equation
C([O:3][C:4]([C@@:6]12[CH2:24][C@H:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:14](=[O:33])[N:13]1[C@@H:9]([CH2:10][CH2:11][CH2:12]1)[C:8](=[O:34])[NH:7]2)=[O:5])C.CO.O[Li].O.Cl>C1COCC1.O>[C:29]([O:28][C:26]([NH:25][C@@H:15]1[C:14](=[O:33])[N:13]2[C@@H:9]([CH2:10][CH2:11][CH2:12]2)[C:8](=[O:34])[NH:7][C@@:6]2([C:4]([OH:5])=[O:3])[C@@H:23]([CH2:24]2)[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 86611241HCID 86611241, compound

Product 1

HCID 86611240HCID 86611240, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The macrocyclic ester 1e from Step C (1.0 g, 2.1 mmol) was first dissolved in THF (3.0 mL), then methanol (3.0 mL) and water (1.5 mL) were added, followed by addition of LiOH—H2O (3 equiv). The resulted mixture was stirred for 4 h and concentrated to dryness. The residue was first re-dissolved in water (10 mL), then acidified with aqueous HCl (3.0 N, 2.2 mL, 6.6 mmol). The aqueous was extracted with EtOAc (3×15 mL). The combined organic layers was dried with sodium sulfate and concentrated to give the acid product 1f (0.93 g, 99%). MS (ESI+): 450 [M+1] (5) and 350 [M+1−100] (100).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was first re-dissolved in water (10 mL)
  3. extractionThe aqueous was extracted with EtOAc (3×15 mL)
  4. dry with materialThe combined organic layers was dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db54bb3d56b1429391415c422b0f84b5
Source dataset
uspto-grants-2010_11
Patent number
US07829665B2

Reaction notes

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