Hydrochloric Acid → {(S)-4-({amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-1-[2-(benzyloxycarbonyl-methyl-amino)-ethyl carbamoyl]-butyl}-carbamic acid tert-butyl ester

HRID 2403987Notes

Reaction equation

HRID 2403987 reaction equation
[NH:1]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:2]([C:27](O)=[O:28])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:26])[NH:8][S:9]([C:12]1[C:24]([CH3:25])=[C:23]2[C:17]([O:18][C:19]([CH2:22]2)([CH3:21])[CH3:20])=[C:15]([CH3:16])[C:13]=1[CH3:14])(=[O:11])=[O:10].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:70]([O:77][C:78](=[O:84])[N:79]([CH2:81][CH2:82][NH2:83])[CH3:80])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1.Cl>CN(C=O)C.CCOC(C)=O>[C:33]([O:32][C:30](=[O:31])[NH:1][C@H:2]([C:27](=[O:28])[NH:83][CH2:82][CH2:81][N:79]([C:78]([O:77][CH2:70][C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:84])[CH3:80])[CH2:3][CH2:4][CH2:5][NH:6]/[C:7](/[NH2:26])=[N:8]/[S:9]([C:12]1[C:24]([CH3:25])=[C:23]([CH3:22])[C:17]2[O:18][C:19]([CH3:21])([CH3:20])[CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:10])=[O:11])([CH3:35])([CH3:34])[CH3:36]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18978092Benzyl 2-aminoethyl(methyl)carbamateHCID 178427604HCID 178427604, compound

Product 1

HCID 178427591{(S)-4-({amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-1-[2-(benzyloxycarbonyl-methyl-amino)-ethyl carbamoyl]-butyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Boc-Arg(Pbf)-OH (3.33 g, 6.32 mmol), HATU (2.88 g, 7.58 mmol) and DIEA (7.4 ml, 31.6 mmol) in DMF (40 ml) was maintained at room temperature for 20 min, followed by the addition of compound C hydrochloride (1.45 g, 6.95 mmol). Stirring was continued for additional 1 h. The reaction mixture was diluted with EtOAc (500 ml) and extracted with water (3×75 ml) and brine (75 ml). The organic layer was dried over MgSO4 and then evaporated to provide compound D (4.14 g, 5.77 mmol) as yellowish amorphous solid. LC-MS [M+H] 717.6 (C35H52N6O8S+H, calc: 717.9).

Workup

  1. extractionextracted with water (3×75 ml) and brine (75 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-6e068937be3b47f4a013ff690826ec18
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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