Diisopropylethylamine → 2-({3-bromo-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-6-S-methyl-1-phenyl-6-thio-D-xylo-hexitol

HRID 1071830Notes

Reaction equation

HRID 1071830 reaction equation
FC(F)(F)C([O-])=O.[NH2:8][C@H:9]([C@@H:17]([OH:24])[C@@H:18]([OH:23])[CH2:19][CH2:20][S:21][CH3:22])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:25][C:26]1[CH:27]=[C:28]([C:35]([N:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])=[O:36])[CH:29]=[C:30]([CH:34]=1)[C:31](O)=[O:32].CCN(C(C)C)C(C)C>>[Br:25][C:26]1[CH:34]=[C:30]([CH:29]=[C:28]([C:35]([N:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])=[O:36])[CH:27]=1)[C:31]([NH:8][C@H:9]([C@H:17]([C@@H:18]([CH2:19][CH2:20][S:21][CH3:22])[OH:23])[OH:24])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:32]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 112903703-Bromo-5-[(dipropylamino)carbonyl]Benzoic AcidHCID 69747529(2s,3r,4s)-2-Amino-6-methylsulfanyl-1-phenyl-hexane-3,4-diol

Product 1

HCID 590672852-({3-bromo-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-6-S-methyl-1-phenyl-6-thio-D-xylo-hexitol

Procedure

The trifluoroacetate salt of (2S,3R,4S)-2-Amino-6-methylsulfanyl-1-phenyl-hexane-3,4-diol (0.1 mmol) was reacted with 5-bromo-N,N-dipropyl-isophthalamic acid as described in method A (addition of an extra equivalent of DIEA to neutralize the amine salt) to give 2-({3-bromo-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-6-S-methyl-1-phenyl-6-thio-D-xylo-hexitol. MS (ESI+) for C27H37BrN2O4S m/z 567 (M+H)+.

Sources & evidence

ORD record
ord-3fc1654fff01438fbc4434d88343cea9
Source dataset
uspto-grants-2005_06
Patent number
US06906104B2

Reaction notes

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