Dimethylformamide → Boc-Thz-Valol

HRID 427381Notes

Reaction equation

HRID 427381 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH:16]1C=CC2N(O)N=NC=2C=1.CCN=C=N[CH2:31][CH2:32][CH2:33][N:34](C)C.Cl.CN([CH:41]=[O:42])C>C(N(CC)CC)C>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([NH:34][C@H:33]([CH2:41][OH:42])[CH:32]([CH3:16])[CH3:31])=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 131722961Boc-Thz-Valol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Deprotection of 94 mg of the compound obtained by the process 1 was performed similarly to that in Example 30 (Process 2), and the obtained product was dissolved in 3 ml of DMF and neutralized with 88.9 μl of triethylamine under ice cooling. To the neutralized solution, 164 mg of Boc-Thz-OH, 108 mg of HOBt and 147 mg of EDC hydrochloride were added and the resultant mixture was stirred for 2 hr. The reaction mixture was treated similarly to that in Example 132 (Process 1) to give 50 mg of the title compound.

Workup

  1. additionThe reaction mixture was treated similarly to that in Example 132 (Process 1)

Sources & evidence

ORD record
ord-7a84ee4197d64415b9fd8d762fae875d
Source dataset
uspto-grants-2001_11
Patent number
US06313094B1

Reaction notes

Loading…