반응 #86669

반응 방정식

DIPEA

43

(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid

amine

(S)-2-Amino-but-3-enoic acid methyl ester hydrochloride

HATU

→

(S)-2-((S)-2-{(S)-3-(4-Allyloxy-phenyl)-2-[(tert-butoxy-hydroxy-methyl)-amino]-propionylamino}-3-methyl-butyrylamino)-but-3-enoic acid methyl ester

용매

EtOAc

DMF

반응 조건

후처리

1. 1
   기타This was partitioned between EtOAc and 1M hydrochloric acid
2. 2
   세척The organic phase was washed sequentially with 1M hydrochloric acid and brine
3. 3
   건조before being dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
7. 7
   기타to yield a white solid, 0.964 g, 76%

실험 절차

Acid 43 (1.03 g, 2.45 mmol), amine 63 (1.1 equiv) and HATU (1.1 equiv) were dissolved in anhydrous DMF (0.10-0.50M relative to acid). DIPEA was added (4 equiv) and the reaction mixture stirred at rt for 18 h. This was partitioned between EtOAc and 1M hydrochloric acid. The organic phase was washed sequentially with 1M hydrochloric acid and brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 0.964 g, 76%. Rf=0.46 (1/1 EtOAc/(50/70) petroleum ether). m.p. 104-106° C.

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