(2S,3R)-3-(benzyloxy)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid → (2S,3S)-N-(2-Chloro-4-iodo-phenyl)-2-{(R)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

HRID 1433784

反応式

HRID 1433784 の反応式
C(O[C@H](C)[C@H](NC(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)C(O)=O)C1C=CC=CC=1.N[C@H](C1C=CC(OC[C@H](O)CO)=CC=1)C(N[C@@H]([C@H](C1C=CC=CC=1)C)C(NC1C=CC(I)=CC=1Cl)=O)=O.N[C@H](C1C=CC(OC[C@H](O[Si](C)(C)C)CO[Si](C)(C)C)=CC=1)C(N[C@@H]([C@H](C1C=CC=CC=1)C)C(NC1C=CC(I)=CC=1Cl)=O)=O.C(OC(N[C@H](C1C=CC(OC[C@H]2COC(C)(C)O2)=CC=1)C(O)=O)=O)(C)(C)C.C[Si](C)(C)[O:144][C@H:145]([CH2:181][O:182][Si](C)(C)C)[CH2:146][O:147][C:148]1[CH:153]=[CH:152][C:151]([C@@H:154]2[C:158](=[O:159])[N:157]([C@@H:160]([C@H:172]([C:174]3[CH:179]=[CH:178][CH:177]=[CH:176][CH:175]=3)[CH3:173])[C:161]([NH:163][C:164]3[CH:169]=[CH:168][C:167]([I:170])=[CH:166][C:165]=3[Cl:171])=[O:162])[C:156](=[O:180])[NH:155]2)=[CH:150][CH:149]=1>>[Cl:171][C:165]1[CH:166]=[C:167]([I:170])[CH:168]=[CH:169][C:164]=1[NH:163][C:161](=[O:162])[C@@H:160]([N:157]1[C:158](=[O:159])[C@@H:154]([C:151]2[CH:150]=[CH:149][C:148]([O:147][CH2:146][C@H:145]([OH:144])[CH2:181][OH:182])=[CH:153][CH:152]=2)[NH:155][C:156]1=[O:180])[C@H:172]([C:174]1[CH:175]=[CH:176][CH:177]=[CH:178][CH:179]=1)[CH3:173]

参加物

6

反応物 5

HCID 16213170(2S,3R)-3-(benzyloxy)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acidHCID 67001404(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acidHCID 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 69007291(2S, 3S)-2-{(R)-4-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramideHCID 69007900(2S,3S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide

生成物 1

HCID 17757684(2S,3S)-N-(2-Chloro-4-iodo-phenyl)-2-{(R)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

実験手順

Prepared by the same method as described in example 110 except that (i) (R)-tert-butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid (prepared as described below) was used in place of (R)-tert-butoxycarbonylamino-{4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-acetic acid in step 4, (ii) (2S,3S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide was temporarily protected as (2S,3S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide (performed as described below) prior to performing step 6, and (iii) acid catalyzed hydrolysis of (2S,3S)-2-{(R)-4-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-N-(2-chloro-4-iodo-phenyl)-3-phenyl-butyramide (performed as described below) was performed prior to purification and isolation of (2S,3S)—N-(2-chloro-4-iodo-phenyl)-2-{(R)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide in step 6.

後処理

  1. customPrepared by the same method
  2. customto purification and isolation of (2S,3S)—N-(2-chloro-4-iodo-phenyl)-2-{(R)-4-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide in step 6

出典と根拠

ORDレコード
ord-0fd0bff1c8c8458da6c3d12269eb2003
出典データセット
uspto-grants-2009_11
特許番号
US07612212B2

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