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Acetic Acid → HCID 11949606, Verbindung

HRID 1009979
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009979
C(OC([O:8][NH:9][C:10]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([CH:21]=O)[CH:19]=[CH:20][C:14]=2[CH:13]=1)=[O:11])C)C(C)C.[CH:23]1([O:28][C:29](=[O:50])[C@@H:30]([NH:42]C(OC(C)(C)C)=O)[CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40][NH2:41])=[CH:36][CH:35]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:23]1([O:28][C:29](=[O:50])[C@@H:30]([NH2:42])[CH2:31][CH2:32][O:33][C:34]2[CH:35]=[CH:36][C:37]([CH2:40][NH:41][CH2:21][C:18]3[CH:19]=[CH:20][C:14]4[CH:13]=[C:12]([C:10](=[O:11])[NH:9][OH:8])[S:16][C:15]=4[CH:17]=3)=[CH:38][CH:39]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 57971713HCID 57971713, VerbindungHCID 57994336HCID 57994336, Verbindung

Produkt 1

HCID 11949606HCID 11949606, VerbindungAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11
1,2-Dichloroethane
Lösungsmittel
HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-formyl-benzo[b]thiophene-2-carboxylic acid (1-isobutoxy-ethoxy) amide (Scheme 13) (0.128 g, 0.40 mmol) in DCE (5 ml) was added (S)-4-(4-aminomethyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid cyclopentyl ester (0.156 g, 0.40 mmol) followed by sodium triacetoxyborohydride (0.253 g, 1.1 g mmol) and glacial acetic acid (0.023 ml, 0.40 mmol). After stirring for 18 hours the mixture was quenched using saturated aqueous NaHCO3 solution (5 ml). The organic layer was separated, washed further with saturated aqueous NaHCO3 solution (2×5 ml), dried (MgSO4) and the solvent removed in vacuo to give a yellow residue. The residue was redissolved in a TFA/DCM solution (1:1, 5 ml). After stirring the solution for 45 minutes the solvent was removed in vacuo. Purification by preparative HPLC gave the product as a white solid (0.030 g, 15% yield). LCMS purity 96.1%, m/z 498 [M++H]+, 1H NMR (300 MHz, DMSO), δ: 1.50-1.90 (9H, m, CH2×4, CH), 2.25 (2H, m, CH2), 4.10-4.40 (7H, m, CH2×3, CH), 5.20 (1H, m, CH), 6.95 (2H, d, ArH×2, J=8.6 Hz), 7.45 (2H, d, ArH×2, J=8.6 Hz), 7.55 (1H, d, ArH, J=7.8 Hz), 8.00 (2H, m, ArH×2), 8.15 (1H, s, ArH), 8.40 (2H, br s, ArH×2), 9.20 (2H, m ArH×2).

Aufarbeitung

  1. customwas quenched
  2. customThe organic layer was separated
  3. washwashed further with saturated aqueous NaHCO3 solution (2×5 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a yellow residue
  7. stirringAfter stirring the solution for 45 minutes the solvent
  8. customwas removed in vacuo
  9. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fb49772055494e529ab4e749bf0466aa
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973181B2

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