HCID 118379306, compound → HCID 118380270, compound

HRID 708486Notes

Reaction equation

HRID 708486 reaction equation
[N:1]([CH2:4][C:5]1[C:9]([CH2:10][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:8][N:7]([CH2:26][C@@H:27]2[C@H:30]([NH:31][C:32](=[O:68])/[C:33](=[N:47]\[O:48][C:49]3([C:52]([O:54][CH:55]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)[C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[O:53])[CH2:51][CH2:50]3)/[C:34]3[N:35]=[C:36]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[S:37][CH:38]=3)[C:29](=[O:69])[N:28]2[S:70]([OH:73])(=[O:72])=[O:71])[N:6]=1)=[N+]=[N-]>CCOC(C)=O.CCO.[Pd]>[NH2:1][CH2:4][C:5]1[C:9]([CH2:10][N:11]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:8][N:7]([CH2:26][C@@H:27]2[C@H:30]([NH:31][C:32](=[O:68])/[C:33](=[N:47]\[O:48][C:49]3([C:52]([O:54][CH:55]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)=[O:53])[CH2:51][CH2:50]3)/[C:34]3[N:35]=[C:36]([NH:39][C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[S:37][CH:38]=3)[C:29](=[O:69])[N:28]2[S:70]([OH:73])(=[O:71])=[O:72])[N:6]=1

Participants

5

Reactant 1

HCID 118379306HCID 118379306, compound

Product 1

HCID 118380270HCID 118380270, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,3S)-2-((4-(azidomethyl)-5-((bis(tert-butoxycarbonyl)amino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-4-oxoazetidine-1-sulfonic acid (111 mg, 0.11 mmol) in EtOAc (1.1 mL) and EtOH (0.22 mL) under N2 was added Pd—C (22 mg, 0.021 mmol). The system was evacuated and backfilled with H2 (3×). After stirring at rt for 4 h, the reaction mixture was filtered through celite with EtOAc and EtOH wash. The filtrate was concentrated in vacuo to afford the title compound (assumed quantitative). The crude residue was used as such in the following step. LCMS: Rt=1.06 min, m/z=1025.7 (M+1), Method 2m_acidic.

Workup

  1. customThe system was evacuated
  2. filtrationthe reaction mixture was filtered through celite with EtOAc and EtOH
  3. washwash
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-306f0f828cb74e22ac8313c60651c9af
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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