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Triethylamine → HCID 13934655, 화합물

HRID 652083
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HRID 652083 반응식
P(Cl)(=O)[O-].[C:5]1([CH2:11][O:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]([OH:38])[C:21]([N:23]2[CH2:37][CH2:36][CH2:35][C@H:24]2[C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:22])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:55]([O:63][CH:64]([P:69](OC)([O:71][CH:72](NC(OCC1C=CC=CC=1)=O)CCCCC([C@]1(C(OCC2C=CC=CC=2)=O)CCCN1)=O)=[O:70])[CH2:65][CH2:66][CH2:67][CH3:68])(=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>C(Cl)Cl>[C:55]([O:63][CH:64]([P:69]([O:71][CH3:72])([O:38][C@@H:20]([CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:13]([O:12][CH2:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:14])[C:21]([N:23]1[CH2:37][CH2:36][CH2:35][C@H:24]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:22])=[O:70])[CH2:65][CH2:66][CH2:67][CH3:68])(=[O:62])[C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 13934652HCID 13934652, 화합물HCID 131715172HCID 131715172, 화합물HCID 178527057HCID 178527057, 화합물

생성물 1

HCID 13934655HCID 13934655, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

The resulting crude phosphonochloridate is taken up in dry methylene chloride (2 ml.) and added dropwise to a methylene chloride (8 ml.) solution of 1-[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-hydroxy-1-oxohexyl]-L-proline, phenylmethyl ester (1.97 g., 4.2 mmole), triethylamine (0.66 g., 6.5 mmole) and dimethylaminopyridine (0.1 g.) at 0° under argon and stirred at 0°-15° for 2 hours. The mixture is partitioned between methylene chloride and 5% potassium bisulfate. The organic phase is washed with brine, dried over magnesium sulfate, and evaporated to dryness. The resulting crude oil is purified by chromatography (LPS-1 silica gel) eluting with (7:3) hexane:acetone. The product containing fractions are combined and concentrated in vacuo to yield 1.55 g. of 1-[(S)-2-[[[1-(benzoyloxy)pentyl]methoxyphosphinyl]oxy-1-oxo-6-[[(phenylmethoxy)carbonyl]amino]hexyl]-L-proline, phenylmethyl ester.

후처리

  1. customThe mixture is partitioned between methylene chloride and 5% potassium bisulfate
  2. washThe organic phase is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe resulting crude oil is purified by chromatography (LPS-1 silica gel)
  6. washeluting with (7:3) hexane
  7. additionThe product containing fractions
  8. concentrationconcentrated in vacuo
  9. customto yield 1.55 g

출처 및 근거

ORD 기록
ord-e103290f9c364a438419eee0bb8b7838
출처 데이터셋
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04670422

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