L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 58746762, compound

HRID 724640Notes

Reaction equation

HRID 724640 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:53][C@@H:54]([CH2:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]2[S:69](=[O:71])(=[O:70])[NH:68][C:67](=[O:72])[CH:66]=2)=[CH:61][CH:60]=1)[C:55]([OH:57])=[O:56]>CN1CCCC1=O.CS(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]([NH:53][C@@H:54]([CH2:58][C:59]1[CH:60]=[CH:61][C:62]([C:65]2[S:69](=[O:71])(=[O:70])[NH:68][C:67](=[O:72])[CH:66]=2)=[CH:63][CH:64]=1)[C:55]([OH:57])=[O:56])=[O:19])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69597707HCID 69597707, compound

Product 1

HCID 58746762HCID 58746762, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-phenylalanine (98.5 mg, 0.371 mmol) in N-methylpyrrolidinone (2.2 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (128 mg, 0.337 mmol) and N,N-diisopropylethylamine (180 μL, 0.001 mol) and premixed for 5 minutes. To the solution was added (2S)-2-amino-3-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoic acid (100 mg, 0.338 mmol) with several drops of DMSO to dissolve and the mixture was stirred overnight. The product was purified by preparative LCMS to afford the desired product (96 mg, 52%). 1H NMR (400 MHz, CD3OD): δ 7.81 (d, J=8.2, 2H), 7.42 (d, J=8.2, 2H), 7.18–7.36 (m, 5H), 6.98 (s, 1H), 4.70–4.73 (m, 1H), 4.26–4.30 (m, 1H), 3.02–3.13 (m, 3H), 2.71–2.76 (m, 1H), 1.33 (s, 9H); LCMS found for C26H9N3O8SNa (M+Na)+: m/z=566.0.

Workup

  1. additionpremixed for 5 minutes
  2. dissolutionto dissolve
  3. customThe product was purified by preparative LCMS

Sources & evidence

ORD record
ord-dd9a9af1cea54840b95a63725afc0787
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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