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Chemical Structure| 1810001-93-4 Chemical Structure| 1810001-93-4

Structure of DBM-MMAF
CAS No.: 1810001-93-4

Chemical Structure| 1810001-93-4

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Product Details of [ 1810001-93-4 ]

CAS No. :1810001-93-4
Formula : C49H74Br2N6O11
M.W : 1082.95
SMILES Code : OC([C@H](CC1=CC=CC=C1)NC([C@H](C)[C@H]([C@@]2([H])N(CCC2)C(C[C@@H](OC)[C@H]([C@@H](C)CC)N(C)C([C@H](C(C)C)NC([C@H](C(C)C)N(C)C(CCCCCN3C(C(Br)=C(C3=O)Br)=O)=O)=O)=O)=O)OC)=O)=O
English Name :((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(6-(3,4-Dibromo-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-methylhexanamido)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoyl)-L-phenylalanine
MDL No. :MFCD34470386

Safety of [ 1810001-93-4 ]

Application In Synthesis of [ 1810001-93-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1810001-93-4 ]

[ 1810001-93-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 745017-94-1 ]
  • 6-(3,4-dibromo-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid [ No CAS ]
  • (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5R)-4-((S)-2-((S)-2-(6-(3,4-dibromo-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-methylhexanamido)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Procedure: DIPC (34 mg, 0.271 mmol) and DIPEA (35 mg, 0.271 mmol) were added to a solution of 6-(3,4-dibromo-2,5-dioxo-2,5-dihydro-1 H-pyrrol-1 - yl)hexanoic acid (3) (250 mg, 0.677 mmol) in DCM (3 mL) and the resulting solution was stirred for 1 h at room temperature. (S)-2-((2R,3R)-3-((S)-1 -((3R4S,5S)-4-((S)- N,3-Dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy- 5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3- phenylpropanoic acid hydrochloride (MMAF.HCI) (208 mg, 0.271 mmol) was added in 50 mg portions over a 4 hr period and the resulting solution was stirred for a further 16 h. The DCM was removed under vacuum and the residue was purified by preparative HPLC. Lyophilization of the appropriate fractions gave (S)-2-((2R,3R)-3- ((S)-1 -((3R,4S,5S)-4-((S)-2-((S)-2-(6-(3,4-dibromo-2,5-dioxo-2,5-dihydro-1 H-pyrrol-1 - yl)-N-methylhexanamido)-3-methylbutanamido)-N,3-dimethylbutanamido)-3- methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3- phenylpropanoic acid (19) (170 mg, 0.156 mmol, 58percent). 1 H NMR (500 MHz, CDCI3) 7.15-7.26 (m, 5H), 4.60-4.92 (m, 4H), 3.70-4.20 (m, 4H), 3.59-3.63 (m, 2H), 3.39- 3.42 (m, 1 H), 3.26-3.35 (m, 6H), 2.93-3.09 (m, 6H), 2.20-2.60 (m, 6H), 1 .70-2.15 (m, 4H), 1 .61 -1 .69 (m, 8H), 1 .25-1 .37 (m, 3H), 1 .15 (dd, J = 18.5, 7.5 Hz, 2H), 0.81 -1 .05 (m, 20H). LC/MS 4.297 min (5-95percent acetonitrile in water over 5 min), m/z 1083.3 [M+H].
 

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