Methanol → HCID 178462139, compound

HRID 1109819Notes

Reaction equation

HRID 1109819 reaction equation
[OH-].[Na+].CO.[NH:5]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@H:6]([C:19]([NH:21][C@H:22]([C:29]([NH:31][C@@H:32]([C:43]([NH:45][C@H:46]([C:48]([O:50]C)=[O:49])[CH3:47])=[O:44])[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)=[O:30])[CH2:23][C:24]1[N:28]=[CH:27][NH:26][CH:25]=1)=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>O>[NH:5]([C:52]([O:54][C:55]([CH3:56])([CH3:58])[CH3:57])=[O:53])[C@H:6]([C:19]([NH:21][C@H:22]([C:29]([NH:31][C@@H:32]([C:43]([NH:45][C@H:46]([C:48]([OH:50])=[O:49])[CH3:47])=[O:44])[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)=[O:30])[CH2:23][C:24]1[N:28]=[CH:27][NH:26][CH:25]=1)=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178501482HCID 178501482, compound

Product 1

HCID 178462139HCID 178462139, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2N aqueous sodium hydroxide solution (7.5 mL, 15 mmol) was added to a methanol (500 mL) and water solution (200 mL) containing Boc-Lys(Boc)-His-D-Trp-Ala-OMe (10.35 g, 13.7 mmol). After the reaction was allowed to stir overnight at room temperature, HPLC analysis indicated that less than 3% of the starting material remained. The resulting solution was concentrated in vacuo to a volume of approximately 200 mL. Water (100 mL) was added and the pH was adjusted to approximately 12 by addition of 2N sodium hydroxide (1 mL). The resulting solution was extracted with ethyl acetate (2×500 mL). The pH of the aqueous phase was then adjusted to 5 by addition of aqueous HCl which resulted in the precipitation of an oil. The aqueous phase was decanted away from the oil and the oil was then rinsed with water (2×50 mL). This oil was converted to a solid foam upon drying to constant weight in vacuo (5.62 g, 55%). 1H NMR indicated the presence of a single isomer in high purity.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo to a volume of approximately 200 mL
  2. additionWater (100 mL) was added
  3. additionthe pH was adjusted to approximately 12 by addition of 2N sodium hydroxide (1 mL)
  4. extractionThe resulting solution was extracted with ethyl acetate (2×500 mL)
  5. additionThe pH of the aqueous phase was then adjusted to 5 by addition of aqueous HCl which
  6. customresulted in the precipitation of an oil
  7. customThe aqueous phase was decanted away from the oil
  8. washthe oil was then rinsed with water (2×50 mL)
  9. customupon drying to constant weight in vacuo (5.62 g, 55%)

Sources & evidence

ORD record
ord-096ae75abfe140788eda9443ef7f5c5a
Source dataset
uspto-grants-1994_06
Patent number
US05322931

Reaction notes

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