Hydroxylamine → HCID 22615023, compound

HRID 843119Notes

Reaction equation

HRID 843119 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[O:22][C:23]5[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][C:37]6[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=6)[C:24]=5[C:25]=4[CH3:26])=[CH:15][C:13]=3[CH:14]=2)=[O:9])[CH2:4][CH2:3]1.[CH3:43][C:44]1C2C(OCCCNCC3C=NC=CC=3)=CC=CC=2OC=1COC1C=CC2OC(C(N3CCNCC3)=O)=CC=2C=1.[BH4-].[Na+].C([BH3-])#N.[Na+].[CH2:90]([O:92][C:93]([C:95]1[O:96][C:97]2[CH:103]=[CH:102][C:101]([O:104][CH2:105][C:106]3[O:107][C:108]4[CH:115]=[CH:114][CH:113]=[C:112]([O:116][CH2:117][CH2:118][CH2:119][NH:120][CH2:121][C:122]5[CH:123]=[N:124][CH:125]=[CH:126][CH:127]=5)[C:109]=4[C:110]=3[CH3:111])=[CH:100][C:98]=2[CH:99]=1)=[O:94])[CH3:91].NO.NN>[O-2].[O-2].[Mn+4]>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[O:22][C:23]5[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:36][C:37]6[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=6)[C:24]=5[C:25]=4[CH3:26])=[CH:15][C:13]=3[CH:14]=2)=[O:9])[CH2:6][CH2:7]1.[CH2:90]([O:92][C:93]([C:95]1[O:96][C:97]2[CH:103]=[CH:102][C:101]([O:104][CH2:105][C:106]3[O:107][C:108]4[CH:115]=[CH:114][CH:113]=[C:112]([O:116][CH2:117][CH2:118][CH2:119][NH:120][CH2:121][C:122]5[CH:123]=[N:124][CH:125]=[CH:126][CH:127]=5)[C:109]=4[C:110]=3[CH:111]3[CH2:44][CH2:43]3)=[CH:100][C:98]=2[CH:99]=1)=[O:94])[CH3:91]

Participants

10

Reactant 7

HCID 787HydroxylamineHCID 9321HydrazineHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 22615023HCID 22615023, compound3×HCID 22615097HCID 22615097, compound2×HCID 68655164HCID 68655164, compound

Product 2

HCID 22615023HCID 22615023, compoundHCID 68655868HCID 68655868, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Aldehyde 34 can be obtained from compound 13 by the reaction using an oxidizing agent such as manganese dioxide. Aldehyde 34 can be the starting material for compounds 35, 36, 37, 38, 39, 40, 41, 42, 43 and 44. Amine 35 can be prepared by the reaction of compound 34 with an amine followed by reduction with a reducing agent such as sodium borohydride and sodium cyanoborohydride. Compounds 36 and 37 can be prepared by the reaction of compound 34 and a hydroxylamine derivative (NH2OR8) and a hydrazine derivative (NH2NR9R10) respectively. Wittig reaction (A. Maercker, Organic Reactions. Vol. 14, PP. 270-490) of compound 34 gives compound 38 and the hydrogenation of compound 38 gives compound 39. Wittig-Honor reaction (J. Boutagy and R. Thomas, Chem. Rev. Vol. 74, PP. 87-99, 1974) of compound 34 gives compound 40. Compound 40 can be converted into compound 41 by hydrogenation over a catalyst such as Palladium on carbon. Compound 41 can be converted into alcohol 42 by reducing compound 41 with a reducing agent such as lithium aluminium hydride. When compound 42 is treated with a base such as sodium hydride and halogen-R61a, compound 43 is obtained. When methanesulfonyl derivative of compound 42, which can be obtained by the reaction of compound 42 and methanesulfonyl chloride in the presence of a base such as triethylamine, is treated with HO—R61b in the presence of a base such as cesium carbonate, compound 44 is prepared.

Workup

  1. customWittig reaction (A

Sources & evidence

ORD record
ord-a1bf92c51f2f40628fc3b723078e81c1
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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