Trifluoroacetic acid → HCID 118380159, compound

HRID 708459Notes

Reaction equation

HRID 708459 reaction equation
C([O:14][C:15]([C:17]1([O:20]/[N:21]=[C:22](/[C:62]2[N:63]=[C:64]([NH:67]C(OC(C)(C)C)=O)[S:65][CH:66]=2)\[C:23]([NH:25][C@@H:26]2[C:29](=[O:30])[N:28]([S:31]([OH:34])(=[O:33])=[O:32])[C@@H:27]2[CH2:35][N:36]2[N:40]=[C:39]([CH2:41][N:42](C(OC(C)(C)C)=O)[CH2:43][CH:44]3[CH2:47][N:46](C(OC(C)(C)C)=O)[CH2:45]3)[CH:38]=[N:37]2)=[O:24])[CH2:19][CH2:18]1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:67][C:64]1[S:65][CH:66]=[C:62](/[C:22](=[N:21]/[O:20][C:17]2([C:15]([OH:16])=[O:14])[CH2:18][CH2:19]2)/[C:23]([NH:25][C@@H:26]2[C:29](=[O:30])[N:28]([S:31]([OH:34])(=[O:32])=[O:33])[C@@H:27]2[CH2:35][N:36]2[N:40]=[C:39]([CH2:41][NH:42][CH2:43][CH:44]3[CH2:47][NH:46][CH2:45]3)[CH:38]=[N:37]2)=[O:24])[N:63]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118380106HCID 118380106, compound

Product 1

HCID 118380159HCID 118380159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Followed the general procedure for the acid mediated deprotection using (2R,3S)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-((4-(((tert-butoxycarbonyl)((1-(tert-butoxycarbonyl)azetidin-3-yl)methyl)amino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonic acid (130 mg, 0.122 mmol), TFA (0.56 mL, 7.32 mmol), and DCM (1.5 mL). 6.3 mg. LCMS: Rt=0.47 min, m/z=599.3 (M+1). Method 2m_acidic_polar. 1H NMR (400 MHz, D2O) δ 7.82 (s, 1H), 7.10 (s, 1H), 5.61 (d, J=5.9 Hz, 1H), 5.01 (q, J=5.6 Hz, 1H), 4.95-4.85 (m, 2H), 4.36 (s, 2H), 4.26-4.15 (m, 2H) 4.11-3.97 (m, 2H), 3.46-3.30 (m, 3H), 1.26 (s, 2H), 1.20-1.05 (m, 2H).

Sources & evidence

ORD record
ord-87d4df5f8deb472b810b32de7f49d5d4
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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