Ammonia → HCID 178433194, compound

HRID 611603Notes

Reaction equation

HRID 611603 reaction equation
[NH:1]([C:5]1[S:6][C:7]([C:11]([N:13]2[CH2:17][CH2:16][C@@H:15]([CH2:18][O:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[CH2:14]2)=[O:12])=[C:8]([CH3:10])[N:9]=1)[C:2]([NH2:4])=[NH:3].FC(F)(F)C([O-])=O.N>O>[NH:1]([C:5]1[S:6][C:7]([C:11]([N:13]2[CH2:17][CH2:16][C@@H:15]([CH2:18][O:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:14]2)=[O:12])=[C:8]([CH3:10])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 84468TrifluoroacetateHCID 178433195HCID 178433195, compound

Product 1

HCID 178433194HCID 178433194, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

140 mg of tert.-butyl (R)-[1-(2-guanidino-4-methyl-thiazole-5-carbonyl)-pyrrolidin-3-ylmethoxy]-acetate are reacted as in Example 6. The crude trifluoroacetate is dissolved in water, neutralized with dilute NH3, purified on Kieselgel 100 C18 -reverse phase and lyophilized from water. There are obtained 99 mg of (R)-[1-(2-guanidino-4-methyl-thiazole-5-carbonyl)-pyrrolidin-3-ylmethoxy]-acetic acid, m.p. 136° C. (sintering), [α]D =+14.2°, (H2O, c=0.5), MS: 342 (M+H)+.

Workup

  1. custompurified on Kieselgel 100 C18 -reverse phase

Sources & evidence

ORD record
ord-ad059994e92645e78d418a877c068381
Source dataset
uspto-grants-1999_12
Patent number
US06001855

Reaction notes

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