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Hydrochloric Acid → N-{(2R,3R)-3-methoxy-3-[(2S)-1-{(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]-L-phenylalanine

HRID 2282921
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HRID 2282921 반응식
C1C2C(COC([NH:18][C@H:19]([C:23]([N:25]([CH3:62])[C@@H:26]([C@@H:58]([CH3:61])[CH2:59][CH3:60])[C@H:27]([O:56][CH3:57])[CH2:28][C:29]([N:31]3[CH2:35][CH2:34][CH2:33][C@H:32]3[C@H:36]([O:54][CH3:55])[C@@H:37]([CH3:53])[C:38]([NH:40][C@H:41]([C:49]([O:51]C)=[O:50])[CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:39])=[O:30])=[O:24])[CH:20]([CH3:22])[CH3:21])=O)C3C(=CC=CC=3)C=2C=CC=1.[OH-].[Li+].O.Cl>C1COCC1>[CH3:55][O:54][C@@H:36]([C@@H:32]1[CH2:33][CH2:34][CH2:35][N:31]1[C:29](=[O:30])[CH2:28][C@@H:27]([O:56][CH3:57])[C@@H:26]([N:25]([CH3:62])[C:23](=[O:24])[C@H:19]([CH:20]([CH3:21])[CH3:22])[NH2:18])[C@@H:58]([CH3:61])[CH2:59][CH3:60])[C@@H:37]([CH3:53])[C:38]([NH:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:39]
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참가 물질

6

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HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86685782methyl N-{(2R,3R)-3-[(2S)-1-{(3R,4S,5S)-4-[{N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoyl}pyrrolidin-2-yl]-3-methoxy-2-methylpropanoyl}-L-phenylalaninate

생성물 1

HCID 86685781
N-{(2R,3R)-3-methoxy-3-[(2S)-1-{(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]-L-phenylalanine
수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirring solution of #113 (2.10 g, 2.46 mM) in 10 mL of THF, lithium hydroxide (228 mg, 5.16 mM) was added followed by 3 mL of water. The reaction was allowed to stir at room temperature for 2 hours. The reaction was acidified though the addition of 1 M HCl and then concentrated in vacuo. The resulting white solid was taken up in 20 mL of acetonitrile and mL of water. The aqueous layer removed and the organic layer was washed once with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Ethyl acetate (20 mL) was then added and the crude solid was allowed to stir for 30 minutes, before being filtered to yield a white solid #250 (1.42 g, 94%). LC-MS (Protocol Q): m/z 619.5 [M+H+], retention time=1.10 minutes. HPLC (Protocol A at 45° C.) m/z 619.4 [M+H+], retention time=6.732 minutes.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe aqueous layer removed
  3. washthe organic layer was washed once with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionEthyl acetate (20 mL) was then added
  8. stirringto stir for 30 minutes
  9. filtrationbefore being filtered

출처 및 근거

ORD 기록
ord-0260b96b35004201b8dc600551f9b43f
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09138486B2

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