Dimethyl Sulfoxide → 6-Benzyloxy-2(S)-tert-butoxycarbonylamino-4,4-dimethyl-hexanal

HRID 863238Notes

Reaction equation

HRID 863238 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:25])([CH3:24])[CH2:12][C@H:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(C(OCC)=O)C1)=O)CCC>C(N(CC)CC)C>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:25])([CH3:24])[CH2:12][C@H:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 22882578((S)-5-benzyloxy-1-hydroxymethyl-3,3-dimethyl-pentyl)-carbamic acid tert-butyl esterHCID 1317205115(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-ethoxycarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 228825796-Benzyloxy-2(S)-tert-butoxycarbonylamino-4,4-dimethyl-hexanal

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound is prepared starting from 28.1 g of 6-benzyloxy-2(S)-tert-butoxycarbonylamino-4,4-dimethyl-hexan-1-ol, 10.5 ml of oxalyl chloride, 11.4 ml of dimethyl sulfoxide and 45 ml of triethylamine analogously to Example 1g): Rf (A)=0.62; Rt (I)=28.1 min; FAB-MS: (M+H)+ =350.

Sources & evidence

ORD record
ord-b04bcb4eec7c465dbe0f6ffff256e99b
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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