Trifluoroacetic acid → HCID 131722190, compound

HRID 1859031Notes

Reaction equation

HRID 1859031 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][NH:21][C:22]([C:24]1[S:28][C:27]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]2[NH:35][CH2:36][CH2:37][N:38]=2)=[N:26][N:25]=1)=[O:23])[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[OH:45][C:39]([C:41]([F:44])([F:43])[F:42])=[O:40].[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][NH:21][C:22]([C:24]1[S:28][C:27]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]2[NH:35][CH2:36][CH2:37][N:38]=2)=[N:26][N:25]=1)=[O:23])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70295004HCID 70295004, compound

Product 1

HCID 131722190HCID 131722190, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl 2(S)-benzyloxycarbonylamino-3-[[2-[4-[(N-imidazolin-2-yl)amino]butyl]-1,3,4-thiadiazol-5-yl]carbonyl]aminopropionate (100 mg, 0.18 mmol) was dissolved in CH2Cl2 containg 0.25 mL of TFA. The solution was stirred at rt for 24 hrs. Concentration gave the product(80 mg, 89% yield). 1H NMR(300 MHz, DMSO-d6)δ1.56(m, 2H), 1.86(m, 2H), 3.18(m, 4H), 3.54(m, 1H), 3.58(s, 4H), 3.66(m, 1H), 4.10(m, 1H), 5.00(s, 2H), 7.30(m, 5H), 7.76(d, 1H), 8.16(t, 1H), 9.10(t, 1H); MS(ESI) Calc. for (M+1)+ : 491. Found: 491.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-524b6413e1dd48178908d5d8c1028f8b
Source dataset
uspto-grants-2000_11
Patent number
US06153628

Reaction notes

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