تفاعل #11101

ord-060cc32606934662a50b466e7bc01a34

معادلة التفاعل

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C
intermediate 38d
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C
(6R,8S)-{3-(allyl-benzyloxycarbonyl-amino)-6-[4-(benzyloxycarbonylamino-imino-methyl)benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl}-acetic acid tert-butyl ester
→
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O
intermediate 39a
المردود 102.0%
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O
(6R,8S)-{3-(allyl-benzyloxycarbonyl-amino)-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl}-acetic acid
المردود 102.0%

المتفاعلات

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C
intermediate 38d
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)OC(C)(C)C
(6R,8S)-{3-(allyl-benzyloxycarbonyl-amino)-6-[4-(benzyloxycarbonylamino-imino-methyl)benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl}-acetic acid tert-butyl ester

الكواشف

لا شيء

المذيبات

C1COCCO1.Cl
HCl dioxane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe solvent was removed in vacuo
  2. 2
    أخرىthe compound was triturated with ether

الإجراء التجريبي

A solution of intermediate 38d (262.3 mg, 0.34 mmol) in 5 mL 4M HCl dioxane was stirred at rt for 2 h. The solvent was removed in vacuo, then the compound was triturated with ether to afford 245 mg (100%) of intermediate 39a. MS (ESI) 707.4 (M+H+), 705.3 (M−H+).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07094783B2uspto-grants-2006_08