Lithium Hydroxide → HCID 23520121, compound

HRID 2252473Notes

Reaction equation

HRID 2252473 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:50]([OH:52])=O)[CH:16]=[C:17]2[C:21]=1[N:20]([CH2:22][CH2:23][CH2:24][NH:25][C:26]1[N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:28]=[CH:29][N:30]=1)[N:19]=[CH:18]2)=O)(C)(C)C.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:86][CH2:87][C@H:88]([NH:93][S:94]([C:97]1[C:102]([CH3:103])=[CH:101][C:100]([CH3:104])=[CH:99][C:98]=1[CH3:105])(=[O:96])=[O:95])[C:89]([O:91]C)=[O:90].[Li+].[OH-]>C1COCC1>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:50]([NH:86][CH2:87][C@H:88]([NH:93][S:94]([C:97]2[C:102]([CH3:103])=[CH:101][C:100]([CH3:104])=[CH:99][C:98]=2[CH3:105])(=[O:96])=[O:95])[C:89]([OH:91])=[O:90])=[O:52])[CH:16]=[C:17]2[C:21]=1[N:20]([CH2:22][CH2:23][CH2:24][NH:25][C:26]1[NH:30][CH:29]=[CH:28][N:27]=1)[N:19]=[CH:18]2

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22598957HCID 22598957, compoundHCID 23520133HCID 23520133, compound

Product 1

HCID 23520121HCID 23520121, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(3-[(tert-butoxy)carbonylamino]-propoxy}-1-(3-([1-(triphenylmethyl)imidazol-2-yl]amino)propyl)-1H-indazole-5-carboxylic acid is treated with Hunig's base and HBTU, then is stirred for about 10 min. The reaction mixture is treated with methyl 3-amino-2(S)-(2,4,6-trimethyl-benzenesulfonyl)aminopropionate. The product is then isolated via chromatography. The methyl ester is saponified using LiOH in THF, and the trityl and boc protecting groups are removed by treatment with trifluoroacetic acid to give the title compound. It is purified by reversed phase preparative HPLC.

Workup

  1. customThe product is then isolated via chromatography
  2. customthe trityl and boc protecting groups are removed by treatment with trifluoroacetic acid

Sources & evidence

ORD record
ord-4eb2a20281634cbb80ddb7e08bbe4a1e
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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