Trifluoroacetic acid → HCID 178513033, compound

HRID 900348Notes

Reaction equation

HRID 900348 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]=[C:16]([NH:50]C(OC(C)(C)C)=O)[NH:17][C@@H:18]([CH2:22][S:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[C:42]4[O:43][C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=5[C:41]=4[CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)[C:19]([OH:21])=[O:20])=O)(C)(C)C>ClCCl>[CH:40]1[C:41]2[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[O:43][C:42]=2[C:37]([C:34]2[CH:33]=[CH:32][C:31]([C:28]3[CH:29]=[CH:30][C:25]([CH2:24][S:23][CH2:22][C@H:18]([NH:17][C:16]([NH2:50])=[NH:15])[C:19]([OH:21])=[O:20])=[CH:26][CH:27]=3)=[CH:36][CH:35]=2)=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454307HCID 178454307, compound

Product 1

HCID 178513033HCID 178513033, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a stirred solution of (2R)-2-[2,3-bis-(tert-butoxycarbonyl)guanidino]-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethylsulfanyl)-propionic acid (250 mg, 0.36 mmol) in anhydrous dichloromethane (10 mL). The reaction was stirred for 4 hours (HPLC control) and then concentrated in vacuo. The resultant brown oil was reconstituted and concentrated from methanol (3×10 mL) and then from dichloromethane (2×10 mL) to give the title compound as an off-white solid (175 mg, 99%): Rf=0.20 (10% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz): δ 8.19 (1H, d, J=8 Hz, Ar—H), 8.13 (1H, d, J=9 Hz, Ar—H), 8.02 (2H, d, J=9 Hz, Ar—H), 7.84 (3H, m, Ar—H), 7.74 (4H, m, 2×Ar—H, 2×NH), 7.53 (3H, m, Ar—H), 7.42 (3H, m, Ar—H), 7.26 (1H, d, J=9 Hz, NH), 7.10 (1H, br s, NH), 4.58 (1H, m, CHN), 3.86 (2H, s, PhCH2S), 2.92 (1H, dd, J=15, 5 Hz, CHHCHN), 2.75 (1H, dd, J=15, 7 Hz, CHHCHN); ESI-LCMS e/z calcd for C29H25N3O3S 495.600, found 496 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. concentrationconcentrated from methanol (3×10 mL)

Sources & evidence

ORD record
ord-a649dedf52504335bf1e06a91dbbfc01
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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