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Sodium cyanoborohydride → 4-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl ester

HRID 1739153
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1739153
Cl.[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH2:23][S:24][CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:27]([NH:34][C@H:35]([CH:57]=O)[CH2:36][S:37][C:38]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C([BH3-])#N.[Na+]>CO>[CH3:2][O:3][C:4](=[O:26])[C@H:5]([CH2:22][CH2:23][S:24][CH3:25])[NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:57][C@@H:35]([NH:34][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:36][S:37][C:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[CH:10][C:9]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
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Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 10388929N-Boc-S-trityl-(L)-cysteinalHCID 69612387(4-Amino-2-phenylbenzoyl)methionine methyl ester hydrochloride

Produkt 1

HCID 183929264-[2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropyl]amino-2-phenylbenzoyl-(S)-methionine methyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a mixture of 4-amino-2-phenylbenzoyl-(S)-methionine methyl ester hydrochloride (1.27 g, 3.22 mmol) in 20 mL of methanol was added N-Boc-S-trityl-(L)-cysteinal (1.0 eq, according to 1H NMR determination of aldehyde percentage) and sodium cyanoborohydride (400 mg, 2.0 eq). The mixture was stirred for 12 hr. After the evaporation of solvents, the residue was extracted with ethyl acetate and concentrated sodium bicarbonate. After removing solvents, the residue was purified through flash column chromatography (1:1=hexane:ethyl acetate, silica) to give the product 1.67 g (yield 67%). 1H NMR (CDCl3) δ 7.65 (d, 8.6 Hz, 1H), 7.34-7.42 (m, 11H), 7.18-7.29 (m, 9H), 6.52 (dd, 2.3 and 8.1 Hz, 1H), 6.34 (d, 2.3 Hz, 1H), 5.65 (d, 7.7 Hz, 1H), 4.64 (ddd, 1H), 4.55 (d, 8.1 Hz, 1H), 4.19 (br t, 1H), 3.78 (br m, 1H), 3.64 (s, 3H), 3.09 (t, 6.1 Hz, 2H), 2.44 (m, 2H), 2.04-2.10 (m, 2H), 2.00 (s, 3H), 1.81-1.90 (m, 1H), 1.60-1.70 (m, 1H), 1.41 (s, 9H); 13C NMR (CDCl3) δ 172.0, 168.3, 155.7, 149.4, 144.3, 141.6, 141.1, 131.3, 129.5, 128.7, 128.5, 127.9, 127.7, 126.8, 122.6, 113.6, 111.3, 79.8, 67.1, 52.2, 51.7, 49.5, 47.2, 34.3, 31.6, 29.4, 28.2, 15.2.

Aufarbeitung

  1. customAfter the evaporation of solvents
  2. extractionthe residue was extracted with ethyl acetate and concentrated sodium bicarbonate
  3. customAfter removing solvents
  4. customthe residue was purified through flash column chromatography (1:1=hexane:ethyl acetate, silica)

Quellen und Nachweise

ORD-Eintrag
ord-ac5840a81c124e2cbd456546ed7fcac6
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05965539

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