Sodium Hydroxide → HCID 178455909, compound

HRID 2081260Notes

Reaction equation

HRID 2081260 reaction equation
[NH:1]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([NH:28][CH2:29][C:30]([NH:32][C@H:33]([C:43]([NH:45][C@H:46]([C:66]([O:68]C)=[O:67])[CH2:47][CH2:48][CH2:49][NH:50][C:51](=[NH:65])[NH:52][S:53]([C:56]1[C:63]([CH3:64])=[CH:62][C:60]([CH3:61])=[CH:59][C:57]=1[CH3:58])(=[O:55])=[O:54])=[O:44])[CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:31])=[O:27])[C@H:22]([CH2:24][CH3:25])[CH3:23])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>O1CCOCC1>[NH:1]([C:70]([O:72][C:73]([CH3:75])([CH3:74])[CH3:76])=[O:71])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([NH:28][CH2:29][C:30]([NH:32][C@H:33]([C:43]([NH:45][C@H:46]([C:66]([OH:68])=[O:67])[CH2:47][CH2:48][CH2:49][NH:50][C:51](=[NH:65])[NH:52][S:53]([C:56]1[C:63]([CH3:64])=[CH:62][C:60]([CH3:61])=[CH:59][C:57]=1[CH3:58])(=[O:55])=[O:54])=[O:44])[CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:31])=[O:27])[C@H:22]([CH2:24][CH3:25])[CH3:23])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178455910HCID 178455910, compound

Product 1

HCID 178455909HCID 178455909, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.14 g (0.13 mmol) of the product (XV) was dissolved in 1.95 ml of dry dioxane and 0.65 ml of 1N NaOH was added thereto. The mixture was stirred at room temperature for 3 hours. After removing the dioxane by concentrating under reduced pressure, approximately 20 ml of water was added and a small amount of insoluble matter was filtered off. The filtrate was cooled and 10% citric acid at 0° C. was added thereto. The precipitate thus formed was filtered, washed with a small amount of water twice and then dried. Thus 0.10 g of Boc-Tyr(Bzl)-Ile-Gly-Ser(Bzl)-Arg(Mts)-OH was obtained. This product was stirred in 6.0 ml of dry dioxane and 6.0 ml of 4N HCl/dioxane for 3 hours to remove the Boc group. Thus 0.08 g of HCl.H-Tyr(Bzl)-Ile-Gly-Ser(Bzl)-Arg(Mts)-OH was obtained.

Workup

  1. customAfter removing the dioxane
  2. concentrationby concentrating under reduced pressure, approximately 20 ml of water
  3. additionwas added
  4. filtrationa small amount of insoluble matter was filtered off
  5. temperatureThe filtrate was cooled
  6. addition10% citric acid at 0° C. was added
  7. customThe precipitate thus formed
  8. filtrationwas filtered
  9. washwashed with a small amount of water twice
  10. customdried

Sources & evidence

ORD record
ord-79b38e1d893c4986bd5e24b8bf76beab
Source dataset
uspto-grants-1993_02
Patent number
US05183804

Reaction notes

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