tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate → HCID 178444782, compound

HRID 495041Notes

Reaction equation

HRID 495041 reaction equation
C([O:5][C:6](=[O:37])[C@H:7]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)[NH:8][C:9]1[C:13]([N:14]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:12][S:11](=[O:28])(=[O:27])[N:10]=1)(C)(C)C>C(O)=O>[CH2:15]([N:14]([C:13]1[C:9]([NH:8][C@H:7]([C:6]([OH:37])=[O:5])[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[N:10][S:11](=[O:27])(=[O:28])[N:12]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 1

HCID 178444783tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 178444782HCID 178444782, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

N-(4-(N,N-Di-n-hexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester (100 mg, 0.19 mmol) was dissolved in formic acid and the mixture stirred at room temperature for 36 hrs. Excess formic acid was removed under reduced pressure to yield N-(4-(N,N-Di-n-hexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl)-L-tyrosine as a white solid (90 mg, 98%). Anal. Calc'd for C23H36N4O5S: C, 57.48; H, 7.55; N, 11.66. Found: C, 57.04; H, 7.23; N, 11.38.

Workup

  1. customExcess formic acid was removed under reduced pressure

Sources & evidence

ORD record
ord-e9ea09d88cde414bb2e8bb7ed5d12bbc
Source dataset
uspto-grants-2009_05
Patent number
US07538215B2

Reaction notes

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