(2S,3R)-3-(benzyloxy)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid → (3S)-N-(4-Ethynyl-2-fluoro-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

HRID 1433791

반응식

HRID 1433791 반응식
[CH2:1]([O:8][C@H](C)[C@H](NC(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)C(O)=O)C1C=CC=CC=1.N[C@@H]([C@H](C1C=CC=CC=1)C)C(NC1C=CC(I)=CC=1F)=O.[NH2:54][C@@H:55]([C@H:72]([C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)[CH3:73])[C:56]([NH:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]#[C:66][Si](C)(C)C)=[CH:61][C:60]=1[F:71])=[O:57].[NH2:80][C@H:81]([C:105]1[CH:110]=[CH:109][C:108]([O:111][CH2:112][C@H:113]([OH:116])CO)=[CH:107][CH:106]=1)[C:82](N[C@@H]([C@H](C1C=CC=CC=1)C)C(NC1C=CC(I)=CC=1Cl)=O)=[O:83]>>[C:65]([C:62]1[CH:63]=[CH:64][C:59]([NH:58][C:56](=[O:57])[CH:55]([N:54]2[C:82](=[O:83])[C@@H:81]([C:105]3[CH:106]=[CH:107][C:108]([O:111][CH2:112][CH2:113][OH:116])=[CH:109][CH:110]=3)[NH:80][C:1]2=[O:8])[C@H:72]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH3:73])=[C:60]([F:71])[CH:61]=1)#[CH:66]

참가 물질

5

반응물 4

HCID 16213170(2S,3R)-3-(benzyloxy)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acidHCID 68618997HCID 68618997, 화합물HCID 69006543(2S,3S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramideHCID 69007467(2S, 3S)-2-amino-N-(2-fluoro-4-trimethylsilanylethynyl-phenyl)-3-phenyl-butyramide

생성물 1

HCID 57935085(3S)-N-(4-Ethynyl-2-fluoro-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

실험 절차

Prepared by the same method as described in example 48 except that (i) after step 3, and prior to step 4, (2S,3S)-2-amino-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide was converted to (2S,3S)-2-amino-N-(2-fluoro-4-trimethylsilanylethynyl-phenyl)-3-phenyl-butyramide under the conditions described below, and (ii) after initial purification in step 6 the product was subjected to chiral HPLC separation as described below. The trimethylsilyl group introduced in step 3 was subsequently removed during step 5 of the synthesis, concomitant with removal of the tert-butyloxycarbonyl protecting group.

후처리

  1. customPrepared by the same method
  2. custompurification in step 6 the product
  3. customwas subjected to chiral HPLC separation
  4. additionThe trimethylsilyl group introduced in step 3
  5. customwas subsequently removed during step 5 of the synthesis, concomitant with removal of the tert-butyloxycarbonyl protecting group

출처 및 근거

ORD 기록
ord-967bdf41824e468bbf445ec54d7e36c4
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612212B2

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