Triethylamine → Methyl 3-((2-(tert-butoxy)-2-oxoethyl)amino)propanoate

HRID 841134노트

반응식

HRID 841134 반응식
C(OC(N[C@@H](CC1N=CNC=1)C(N(CC(NCC(C)(C1C=CC=CC=1)C)=O)CCC(OC)=O)=O)=O)C1C=CC=CC=1.Cl.[CH3:43][O:44][C:45](=[O:49])[CH2:46][CH2:47][NH2:48].Br[CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53].C(N(CC)CC)C>C(Cl)Cl>[CH3:43][O:44][C:45](=[O:49])[CH2:46][CH2:47][NH:48][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 178500811methyl 3-([(2S)-2-[(benzyloxy)carbonyl]amino-3-(1H-4-imidazolyl)propanoyl]-2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethylamino)propanoate

생성물 1

HCID 14845245Methyl 3-((2-(tert-butoxy)-2-oxoethyl)amino)propanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Scheme 2 shows a method by which the compounds of the present invention can be prepared, by illustrating the synthesis of Example 4, methyl 3-([(2S)-2-[(benzyloxy)carbonyl]amino-3-(1H-4-imidazolyl)propanoyl]-2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethylamino)propanoate. Reaction of β-alanine methyl ester hydrochloride with t-butyl bromoacetate was carried out in methylene chloride in the presence of triethylamine as the base to give 3-(tert-butoxycarbonylmethyl-amino)-propionic acid methyl ester which was then coupled to Cbz-His(trityl) in methylene chloride/acetonitrile with HBTU as coupling agent, and triethylamine as the base. The resulting product was treated with 95% aqueous TFA, to remove the trityl and the t-butyl groups, followed by coupling with β,β-dimethylphenethylamine in methylene chloride/dimethylformamide, with HBTU as coupling agent, and diisopropylethylamine as the base to give the desired product.

후처리

  1. customcan be prepared

출처 및 근거

ORD 기록
ord-8b23c1fd0839421c861e190ede72455b
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369034B1

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