Hydrochloric Acid → HCID 178495676, compound

HRID 1751680Notes

Reaction equation

HRID 1751680 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:56]([CH3:58])[CH3:57])[C:7]([N:9]1[CH2:13][C@@H:12]([CH3:14])[CH2:11][C@H:10]1[C:15]1[NH:19][C:18]2[C:20]3[C:25]([CH:26]=[CH:27][C:17]=2[N:16]=1)=[CH:24][C:23]([C:28]1[CH:29]=[C:30]2[C:53](=[CH:54][CH:55]=1)[C:34]1[NH:35][C:36]([C@@H:38]4[CH2:42][C@H:41]([CH2:43][O:44][CH3:45])[CH2:40][N:39]4C(OC(C)(C)C)=O)=[N:37][C:33]=1[CH:32]=[CH:31]2)=[CH:22][CH:21]=3)=[O:8])=[O:4].Cl.[CH3:60][O:61][C@H:62]([CH3:72])[C@H:63]([NH:67][C:68]([O:70][CH3:71])=[O:69])[C:64]([OH:66])=O.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>C(Cl)Cl.CN(C=O)C>[CH3:71][O:70][C:68]([NH:67][C@@H:63]([C@H:62]([O:61][CH3:60])[CH3:72])[C:64]([N:39]1[CH2:40][C@@H:41]([CH2:43][O:44][CH3:45])[CH2:42][C@H:38]1[C:36]1[NH:35][C:34]2[C:53]3[C:30]([CH:31]=[CH:32][C:33]=2[N:37]=1)=[CH:29][C:28]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[C:18]1[NH:19][C:15]([C@@H:10]4[CH2:11][C@H:12]([CH3:14])[CH2:13][N:9]4[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:56]([CH3:58])[CH3:57])=[N:16][C:17]=1[CH:27]=[CH:26]2)=[CH:55][CH:54]=3)=[O:66])=[O:69]

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 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acidHCID 178495677HCID 178495677, compound

Product 1

HCID 178495676HCID 178495676, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-tert-Butyl 2-(2′-((2S,4S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-methylpyrrolidin-2-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate (120 mg, 0.152 mmol) was dissolved in DCM (5 mL) and treated with HCl (4.0 mL in dioxane, 1 mL). After stirring for 1 h, the reaction mixture was concentrated under reduced pressure. The crude residue was treated with (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (35 mg, 0.18 mmol), HATU (69 mg, 0.18 mmol), DMF (1 mL) and DIPEA (0.26 mL, 1.5 mmol). After 20 min, the reaction was quenched with water. The product was purified by reverse-phase HPLC to afford methyl (S)-1-((2S,4S)-2-(2′-((2S,4S)-1-((2S,3R)-2-methoxycarbonylamino-3-methoxybutanoyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-4-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (120 mg). MS (ESI) m/z 862 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. waitAfter 20 min
  3. customthe reaction was quenched with water
  4. customThe product was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-2f91d9cad13c453281d305db7c6ed89d
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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